931-87-3 Usage
Description
Cyclooctene, also known as cis-cyclooctene, is a cyclic alkene compound with a double bond in a cis configuration. It is an organometallic compound that is widely used in various chemical reactions and applications due to its unique structure and properties.
Uses
Used in Organometallic Chemistry:
Cyclooctene is used as a displaced ligand in chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer. These organometallic complexes are important in various chemical reactions and catalysis processes.
Used in Synthetic Chemistry:
Cyclooctene acts as a monomer in synthetic chemistry, allowing for the creation of various complex organic compounds through reactions and polymerizations.
Used in the Preparation of 1-chloro-4-(trichloromethyl) cyclooctane:
Cyclooctene is used to prepare 1-chloro-4-(trichloromethyl) cyclooctane by reacting with carbon tetrachloride using dichlorotris(triphenylphosphine) ruthenium(II) as a catalyst. CYCLOOCTENE has potential applications in various chemical industries.
Used in Surface Chemistry Research:
Cyclooctene is used to study the chemisorption of alkenes on silicon(100) surfaces using scanning tunneling microscopy. This research helps in understanding the interactions between organic molecules and solid surfaces, which is crucial for the development of new materials and technologies.
Synthesis Reference(s)
Journal of the American Chemical Society, 102, p. 2693, 1980 DOI: 10.1021/ja00528a029The Journal of Organic Chemistry, 40, p. 2555, 1975 DOI: 10.1021/jo00905a040Tetrahedron Letters, 14, p. 2667, 1973
Purification Methods
The cis-isomer is freed from the trans-isomer by fractional distillation through a spinning-band column, followed by preparative gas chromatography on a Dowex 710-Chromosorb W GLC column. It is passed through a short alumina column immediately before use [Collman et al. J Am Chem Soc 108 2588 1986]. It has also been distilled in a dry N2 glove box from powdered fused NaOH through a Vigreux column (p 11), then passed through activated neutral alumina before use [Wong et al. J Am Chem Soc 109 4328 1987]. Alternatively it can be purified via the AgNO3 salt. This salt is obtained from crude cyclooctene (40 mL) by shaking at 70-80o with 50% w/w AgNO3 (2 x 15 mL) to remove cyclooctadienes (aqueous layer). Extraction is repeated at 40o (4 x 20 mL, of 50% AgNO3). Three layers are formed each time. The middle layer contains the AgNO3 adduct of cyclooctene which crystallises on cooling the layer to room temperature. The adduct (complex 2:1) is highly soluble in MeOH (at least 1g/mL) from which it crystallises in large flat needles when cooled at 0o. It is dried under slight vacuum for 1 week in the presence of CaCl2 and paraffin wax soaked in cyclooctene. It has m 51o and loses hydrocarbon on exposure to air. cis-Cyclooctene can be recovered by steam distillation of the salt, collected, dried (CaCl2) and distilled in vacuum. [Braude et al. J Chem Soc 4711 1957, AgNO3: Jones J Chem Soc 1808 1954, Cope & Estes J Am Chem Soc 72 1128 1950, Beilstein 5 I 35, 5 IV 263.] FLAMMABLE LIQUID.
Check Digit Verification of cas no
The CAS Registry Mumber 931-87-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 1 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 931-87:
(5*9)+(4*3)+(3*1)+(2*8)+(1*7)=83
83 % 10 = 3
So 931-87-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-
931-87-3Relevant articles and documents
Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis
Zhou, Min-Jie,Zhang, Lei,Liu, Guixia,Xu, Chen,Huang, Zheng
supporting information, p. 16470 - 16485 (2021/10/20)
The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.
Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex
Hara, Naofumi,Nakao, Yoshiaki,Saito, Teruhiko,Seki, Rin
, p. 6388 - 6394 (2021/05/31)
We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.
Unprecedented Selectivity of Ruthenium Iodide Benzylidenes in Olefin Metathesis Reactions
Ivry, Elisa,Lemcoff, N. Gabriel,Nechmad, Noy B.,Phatake, Ravindra,Poater, Albert
, p. 3539 - 3543 (2020/02/04)
The development of selective olefin metathesis catalysts is crucial to achieving new synthetic pathways. Herein, we show that cis-diiodo/sulfur-chelated ruthenium benzylidenes do not react with strained cycloalkenes and internal olefins, but can effectively catalyze metathesis reactions of terminal dienes. Surprisingly, internal olefins may partake in olefin metathesis reactions once the ruthenium methylidene intermediate has been generated. This unexpected behavior allows the facile formation of strained cis-cyclooctene by the RCM reaction of 1,9-undecadiene. Moreover, cis-1,4-polybutadiene may be transformed into small cyclic molecules, including its smallest precursor, 1,5-cyclooctadiene, by the use of this novel sequence. Norbornenes, including the reactive dicyclopentadiene (DCPD), remain unscathed even in the presence of terminal olefin substrates as they are too bulky to approach the diiodo ruthenium methylidene. The experimental results are accompanied by thorough DFT calculations.
