- Biomimetic synthesis toward the transtaganolides/basiliolides
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(Figure Presented) A concise biomimetic approach toward transtaganolides C and D involving an Ireland-Claisen rearrangement/intramolecular Diels-Alder reaction sequence suggesting the involvement of pericyclic reactions in the biosynthesis of these biologically active plant metabolites is presented. A final coupling reaction establishes the carbon framework of the transtaganolides.
- Larsson, Rikard,Sterner, Olov,Johansson, Martin
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Read Online
- Inter- and intramolecular [4 + 1]-cycloadditions between electron-poor dienes and electron-rich carbenes
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Inter- and intramolecular [4 + 1]-annulations between dialkoxy carbenes and electron-deficient dienes afford mono- or bicyclic products in moderate to good yield. Copyright
- Spino, Claude,Rezaei, Hadi,Dupont-Gaudet, Kristina,Belanger, Francis
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Read Online
- Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides
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The first C?SCF3/SeCF3 cross-coupling reactions using gold redox catalysis [(MeDalphos)AuCl], AgSCF3 or Me4NSeCF3, and organohalides as substrates are reported. The new methodology enables a one-stop shop synthesis of aryl/alkenyl/alkynyl trifluoromethylthio- and selenoethers with a broad substrate scope (>60 examples with up to 97 % isolated yield). The method is scalable, and its robustness is evidenced by the late-stage functionalization of various bioactive molecules, which makes this reaction an attractive alternative in the synthesis of trifluoromethylthio- and selenoethers for pharmaceutical and agrochemical research and development.
- Mudshinge, Sagar R.,Yang, Yuhao,Xu, Bo,Hammond, Gerald B.,Lu, Zhichao
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supporting information
(2022/02/10)
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- Compound, preparation method and application of compound in preparation of medicine for treating small cell lung cancer
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The invention provides a compound, a preparation method thereof and an application of the compound in preparation of drugs for treating small cell lung cancer. The structural formula of the compound is shown in the specification, and the compound generates a synergistic effect on small cell lung cancer tumor cells by blocking the activity of PARP and/or XPO1 protein. Researches show that the compound provided by the invention can effectively inhibit proliferation of small cell lung cancer cells in vivo and in vitro, and can be applied to drugs for treating small cell lung cancer.
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Paragraph 0027-0030
(2021/03/13)
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- Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
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Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
- Chen, Violet Yijang,Kwon, Ohyun
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supporting information
p. 8874 - 8881
(2021/03/17)
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- Palladium-catalysed regio- And stereoselective arylative substitution of γ,δ-epoxy-α,β-unsaturated esters and amides by sodium tetraaryl borates
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Palladium-catalysed reactions of γ,δ-epoxy-α,β-unsaturated esters and amides with NaBAr4 reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. A
- Artok, Levent,Bilgi, Yasemin,Ku?, Melih
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supporting information
p. 6378 - 6383
(2020/09/07)
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- Enantioselective Synthesis of α-Chiral Propargylic Silanes by Copper-Catalyzed 1,4-Selective Addition of Silicon Nucleophiles to Enyne-Type α,β,γ,δ-Unsaturated Acceptors
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A copper-catalyzed deconjugative addition of silicon nucleophiles to a broad range of enyne-type α,β,γ,δ-unsaturated acceptors with high enantiocontrol is reported. The method is 1,4-selective with hardly any formation of the 1,6-adduct. The double-bond geometry is shown to be critical for achieving this chemoselectivity: exclusive 1,4-addition for E and predominant 1,6-addition for Z. By this, E-configured enynoates, enynamides, and enynones have been converted to the corresponding α-chiral propargylic silanes with excellent enantiomeric excesses.
- Mao, Wenbin,Oestreich, Martin
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supporting information
p. 8096 - 8100
(2020/11/02)
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- Studies toward the Total Synthesis of the Marine Macrolide Salarin C
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A convergent strategy for the synthesis of dideoxysalarin C (3) as a potential intermediate for the total synthesis of the marine macrolide salarin C (1) is described. The macrolactone core of 3 was assembled by Suzuki coupling between alkyl iodide 9 and
- Schrof, Raffael,Altmann, Karl-Heinz
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supporting information
p. 7679 - 7683
(2018/12/11)
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- Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide
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We report the total synthesis of the natural products isodihydrokoumine and (19Z)-taberpsychine in 11 steps each and (4R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.
- Kerkovius, Jeff K.,Kerr, Michael A.
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supporting information
p. 8415 - 8419
(2018/07/05)
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- Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium
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An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.
- Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa
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supporting information
p. 5856 - 5859
(2017/11/10)
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- Total syntheses of bupleurynol and its analog
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An efficient route to the natural products bupleurynol and its analog (RB-2), isolated from Bupleuri Radix, was established based on versatile intermediate (15). In this synthetic route, Sonogashira and Cadiot–Chodkiewicz coupling as well as Julia–Kociens
- Ma, Kai-Qing,Miao, Yan-Hong,Gao, Xiao-Xia,Chao, Jian-Bin,Zhang, Xiang,Qin, Xue-Mei
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supporting information
p. 1035 - 1038
(2017/05/22)
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- A highly practical approach to chiral homoallylic-homopropargylic amines via aza-Barbier reaction
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The first access to chiral homoallylic-homopropargylic amine bearing two contiguous stereocenters has been well accomplished via zinc-promoted aza-Barbier reaction. N-tert-Butanesulfinyl ketimines are well-tolerated substrates, providing the tertiary amin
- Yuan, Bin-Hua,Zhang, Zhi-Cheng,Liu, Wen-Jie,Sun, Xing-Wen
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supporting information
p. 2147 - 2151
(2016/05/02)
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- Enantioselective Allylation of β-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin
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A comparative study of the catalytic allylations and crotylations of (E)- and (Z)-haloacrylaldehydes by Lewis bases (chiral N,N′-dioxides) and Br?nsted acids (chiral phosphoric acids) was undertaken. The reactions proceeded with high enantio- and diastereoselectivities with slightly better asymmetric induction observed in the case of N,N′-dioxide catalysis. The formed enantioenriched chiral unsaturated haloalcohols could be considered general building blocks, as they could be used in the syntheses of more complex natural products possessing substituted 1,3-diene fragments. This was exemplified by the formal total syntheses of pteronenone and antillatoxin. A comparative study of allylations and crotylations of (E)- and (Z)-haloacrylaldehydes is undertaken under Lewis base and Br?nsted acid catalysis. The reactions proceed in both cases with high enantio- and diastereoselectivities. The formed chiral unsaturated haloalcohols can be considered as general building blocks, as exemplified by the formal total syntheses of pteronenone and antillatoxin; HBPin = pinacolborane.
- Koukal, Petr,Ul?, Jan,Ne?as, David,Kotora, Martin
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supporting information
p. 2110 - 2114
(2016/05/09)
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- Stereoselectivity synthetic method of radix bupleuri alkynol and (2Z,8E,10E)-pentadecane-2,8,10-triene-4,6-diyne-1-ol thereof
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The invention belongs to the technical field of chemical synthesis, and relates to a stereoselectivity synthetic method of radix bupleuri alkynol and (2Z,8E,10E)-pentadecane-2,8,10-triene-4,6-diyne-1-ol thereof. The method comprises the steps that (2E,8Z)
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Paragraph 0047; 0048
(2017/02/23)
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- Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration
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A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organobor
- Faizi, Darius J.,Issaian, Adena,Davis, Ashlee J.,Blum, Suzanne A.
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supporting information
p. 2126 - 2129
(2016/03/05)
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- Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne
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The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated 8(Z),10(E)-diene moiety was achieved through a tethered ring-closing metathesis approach, comprising a Ru-catalyz
- Schmidt, Bernd,Aud?rsch, Stephan
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supporting information
p. 1162 - 1165
(2016/03/15)
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- All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration
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1,3-Enynes containing allylic hydrogens cis to the alkyne function as three-carbon components in rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations to produce spirodialins. The proposed mechanism of these reactions involves the alkenyl-to-ally
- Burns, David J.,Best, Daniel,Wieczysty, Martin D.,Lam, Hon Wai
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supporting information
p. 9958 - 9962
(2015/08/19)
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- Metal-catalyzed formation of 1,3-cyclohexadienes: A catalyst-dependent reaction
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A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was used as the catalyst,
- Zhu, Shifa,Huang, Xiaobing,Zhao, Tian-Qi,Ma, Tongmei,Jiang, Huanfeng
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supporting information
p. 1225 - 1233
(2015/03/04)
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- Heck coupling using a vinyliodo-mida boronate: An efficient and modular access to polyene frameworks
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A simple Heck coupling between an alkenyl iodo-boronate and a variety of terminal olefins is disclosed. This method gives access to a wide range of dienic moieties including valuable bis-functionalized dienes. The synthetic potential of the coupling reaction is demonstrated by a short and modular preparation of several tetraenic compounds.
- Cornil, Johan,Gurinot, Amandine,Cossy, Janine,Echeverria, Pierre-Georges,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
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supporting information
p. 948 - 951
(2015/04/21)
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- Fully substituted pyranones via quasi-heterogeneous genuinely ligand-free migita-stille coupling of iodoacrylates
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Migita-Stille coupling of (Z)-?2-iodoacrylates with (E)-?±-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)4 is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.
- Kratochv??l, Ji????,Nov??k, Zden??k,Ghavre, Mukund,Nov??kov??, Lucie,R????i??ka, Ale??,Kune??, Ji????,Pour, Milan
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supporting information
p. 520 - 523
(2015/03/04)
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- ANTIDIABETIC COMPOUNDS
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Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
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Page/Page column 109; 110
(2015/09/23)
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- Synthesis of cyclic alkenylsiloxanes by semihydrogenation: A stereospecific route to (Z)-alkenyl polyenes
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Cyclic alkenylsiloxanes were synthesized by semihydrogenation of alkynylsilanes - a reaction previously plagued by poor stereoselectivity. The silanes, which can be synthesized on multigram scale, undergo Hiyama-Denmark coupling to give (Z)-alkenyl polyene motifs found in bioactive natural products. The ring size of the silane is crucial: five-membered cyclic siloxanes also couple under fluoride-free conditions, whilst their six-membered homologues do not, enabling orthogonality within this structural motif.
- Elbert, Bryony L.,Lim, Diane S. W.,Gudmundsson, Haraldur G.,O'Hanlon, Jack A.,Anderson, Edward A.
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supporting information
p. 8594 - 8598
(2014/07/21)
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- SYNTHETIC RETINOIDS FOR CONTROL OF CELL DIFFERENTIATION
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The present invention relates to synthetic retinoid compounds of formula (I) and their use in the control of cell differentiation or apoptosis.
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Page/Page column 33-34
(2012/06/30)
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- Palladium-catalyzed alkoxycarbonylation of (Z)-2-en-4-yn carbonates leading to 2,3,5-trienoates
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Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with
- Akpinar, G. Eray,Kus, Melih,Uecuencue, Muhammed,Karakus, Erman,Artok, Levent
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supporting information; experimental part
p. 748 - 751
(2011/04/24)
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- Gold-catalyzed oxidative ring expansions and ring cleavages of alkynylcyclopropanes by intermolecular reactions oxidized by diphenylsulfoxide
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A golden opportunity: A novel gold-catalyzed oxidative ring-expansion of unactivated cyclopropylalkynes using Ph2SO has been developed (see scheme). For substrates bearing a donor group at the cyclopropane ring, preliminary results reveal a distinct cleavage of the cyclopropane unit; such a ring cleavage is further applicable to the synthesis of 2H-pyrans. L=P(tBu) 2(o-biphenyl), Tf=triflate. Copyright
- Li, Chia-Wen,Pati, Kamalkishore,Lin, Guan-You,Sohel, Shariar Md. Abu,Hung, Hsiao-Hua,Liu, Rai-Shung
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supporting information; experimental part
p. 9891 - 9894
(2011/02/24)
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- A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes
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The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans. The Royal Society of Chemistry 2010.
- Bartoli, Giuseppe,Cipolletti, Roberto,Di Antonio, Giustino,Giovannini, Riccardo,Lanari, Silvia,Marcolini, Mauro,Marcantoni, Enrico
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experimental part
p. 3509 - 3517
(2010/08/21)
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- Synthesis of isomeric polyacetylenes based on natural hydroxy matricaria esters
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The construction of a library of natural and related polyacetylenes using a convergent synthetic strategy based on a palladium mediated cross-coupling reaction is described. The systematic synthetic study led to all possible alkene isomers of the hydroxy matricaria esters 29-32, and the corresponding tiglates 1-4. The synthesis of many of these compounds is described for the first time.
- Garrais, Solange,Turkington, Jennifer,Goldring, William P.D.
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experimental part
p. 8418 - 8427
(2009/12/26)
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- Synthesis and cytotoxicity of a salicylihalamide a analogue
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The synthesis of a simple analogue of salicylihalamide A with a truncated lactone ring (±2) was achieved in 10 steps. Its cytotoxicity profile in the NCI 60-cell-line human tumor assay differed significantly from that of salicylihalamide A in both level a
- Tang, Shaoshan,Erickson, Karen L.
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supporting information; experimental part
p. 898 - 901
(2009/04/05)
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- Mechanistic studies on the Heck-Mizoroki cross-coupling reaction of a hindered vinylboronate ester as a key approach to developing a highly stereoselective synthesis of a C1-C7 Z,Z,E,-triene synthon for viridenomycin
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Mechanistic studies of the Heck-Mizoroki reaction of a vinylboronate ester with electronically different (four-substituted) aryl iodides shows that electron donors accelerate the cross-coupling, demonstrating that the oxidative addition step is not rate d
- Batsanov, Andrei S.,Knowles, Jonathan P.,Whiting, Andrew
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p. 2525 - 2532
(2008/02/02)
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- Synthetic studies toward the construction of the cis-decalin portion of superstolides A and B. Application of a sequential double Michael reaction and an anionic oxy-Cope rearrangement
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(Chemical Equation Presented) A highly convergent strategy for the asymmetric synthesis of the cis-decalin portion of the antitumor macrolide superstolide A was developed. The key reactions in our approach involve a sequential double Michael reaction and
- Hua, Zhengmao,Yu, Wensheng,Su, Mei,Jin, Zhendong
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p. 1939 - 1942
(2007/10/03)
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- Synthesis of enamides from aldehydes and amides
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A range of double unsaturated amides (15, 19, and 21), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac2O and pyridine affected clean conversion to the corresponding enamides, such as 42, 45, and 47. Alternatively, N,S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less general. Application of these methods led to the natural products lansiumamide-A (30_cis), lansiumamide-I (31) and lansiumamide-B (32).
- Bayer, Alexander,Maier, Martin E.
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p. 6665 - 6677
(2007/10/03)
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- Total synthesis of (-)-salicylihalamide.
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A concise total synthesis of the potent cytotoxic marine natural products salicylihalamide A and B (la, b) is reported. Key steps of our approach were the asymmetric hydrogenation reactions of beta-keto esters 18 and 32 catalyzed by [((S)-BINAP)Ru-Cl2]2. NEt3 and the cyclization of the macrolide core by ring closing olefin metathesis (RCM) using the "second-generation" ruthenium carbene complex 24 as the catalyst which bears an imidazol-2-ylidene ligand. The EIZ ratio obtained in this macrocyclization reaction was determined by the protecting groups at the remote phenolic OH group of the cyclization precursor. The elaboration of the resulting cycloalkene 37 into the final target involved a CrCl2-mediated synthesis of vinyliodide 49 which, after deprotection, did undergo a copper-catalyzed cross-coupling process with the (Z,Z)-configurated carboxamide 42 to form the labile enamide moiety of 1. Compound 42 was derived from a palladium-catalyzed Negishi coupling between butynylzinc chloride and 3-iodoacrylate 39 followed by a Lindlar reduction of enyne 40 thus obtained and a final aminolysis of the ester group.
- Fuerstner,Dierkes,Thiel,Blanda
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p. 5286 - 5298
(2007/10/03)
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- Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A
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Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethiode auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd.
- Gonzalez, Angel,Aiguade, Josep,Urpi, Felix,Vilarrasa, Jaume
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p. 8949 - 8952
(2007/10/03)
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- A convenient procedure for the efficient preparation of alkyl (Z)-3-iodo-2-alkenoates
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Reaction of alkyl 2-alkynoates with sodium iodide (1.6-5.5 equiv.) in acetic acid (6.2-13 equiv.) at 115 deg C provides good to excellent yields of the corresponding alkyl (Z)-3-iodo-2-alkenoates.
- Piers, Edward,Wong, Timothy,Coish, Philip D.,Rogers, Christine
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p. 1816 - 1819
(2007/10/02)
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- A Novel Regio- and Stereospecific Hydrohalogenation Reaction of 2-Propynoic Acid and Its Derivatives
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2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products.A rationale for the regio- and stereospecifity is briefly discussed.
- Ma, Shengming,Lu, Xiyan,Li, Zhigang
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p. 709 - 713
(2007/10/02)
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- A highly efficient synthesis of (Z) γ-iodo allylic alcohols
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The reaction of (Z) Methy-β-iodo propenoate with diisobutylaluminium hydride and subsequent reaction with a Grignard reagents allows the synthesis of (Z) γ-iodo allylic alcohols in a very easy way. (Chemical Equation Presented).
- Marek, Ilane,Alexakis, Alexandre,Normant, Jean-F.
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p. 5329 - 5332
(2007/10/02)
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- Synthesis and Properties of the Valence Tautomer of cis-Iodosocyclopropanecarboxylic Acid: 4,5-Methano-1-hydroxyiodoxol-3(1H)-one
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4,5-Methano-1-hydroxyiodoxol-3(1H)-one (4) was synthesized from propionic acid in six steps.Key reactions included Simmons-Smith cyclopropanation of cis-3-iodopropen-2-ol, followed by pyridinium dichromate oxidation to cis-iodocyclopropanecarboxylic acid.The final iodo to iodoso oxidation used either chlorination/hydrolysis or peracetic acid procedures.Compound 4 exists in the 1-hydroxyiodoxolone form, not in the "open" cis-cyclopropanecarboxylic acid form (3), as shown by its "high" pKa (7.55) and by its ability to cleave p-(nitrophenyl)diphenyl phosphate(k = 0.0044 s-1) in pH 8 aqueous micellar solution.Compound 4 disproportionates to iodo (5) and iodoxy (7) compounds in pH 8 aqueous buffer with k = 0.027 L/(M*s).Ab initio molecular orbital calculations are described which help rationalize the observed properties of 4.The reactivity of 4 (and related species) is intimately connected to the structure and bonding around the formally hypervalent iodine atom.
- Moss, Robert A.,Wilk, Boguslawa,Krogh-Jespersen, Karsten,Westbrook, John D.
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p. 6729 - 6734
(2007/10/02)
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