90929-16-1Relevant articles and documents
On the isolation of neat allylic fluorides
Lee, Eunsung,Yandulov, Dmitry V.
scheme or table, p. 474 - 483 (2009/12/06)
Neat cinnamyl fluoride, geranyl fluoride, 5-carbomethoxy-3-fluorocyclohexene and parent 3-fluorocyclohexene undergo spontaneous decomposition on contact with borosilicate glass or catalytic quantities of moderately strong acids that consists in polycondensation with elimination of HF initiated by electrophilic abstraction of F-. Acid sensitivity of these allylic fluorides correlates with stability of respective allylic cations, exceeds that of parent benzyl fluoride, yet can be mitigated by the use of Teflon and PFA containers that permit their isolation and handling in the neat state.
The Synthesis and Application of Novel Nitrating And Nitrosating Agents
Hakimelahi, Gholam H.,Sharghi, Hashem,Zarrinmayeh, Hamide,Khalafi-Nezhad, Ali
, p. 906 - 915 (2007/10/02)
Alcohols and phenols are efficiently nitrated with thionyl chloride nitrate or thionyl nitrate, even in the presence of an aromatic moiety.While thionyl chloride nitrate is suitable for nitration of primary OH-groups in carbohydrates, thionyl nitrate is reactive enough to react with secondary OH-groups as well.These reagents permit the highly selective nitration of the 5'-, 2',5'- and 3',5'-OH-groups of ribonucleosides to produce either mono- or diprotected nitro derivatives in high yields.Carbon acids and the enol form of some ketones are efficiently nitrated with trifluoromethanesulfonyl nitrate/potassium tert-butoxide.Lutidine N-oxide(2,6-(CH3)2C5H3N->O) was found to have marked effect on nitration reactions.Similarly, thionyl chloride nitrite and thionyl nitrite exhibit an excellent capacity for nitrosation of the aforementioned substrates
Thallium(III)-Mediated Allylation of Alcohols and Carboxylic Acids: Umpolung of Reactivity of Allylmetal (Group IVb) Compounds
Ochiai, Masahito,Fujita, Eiichi,Arimoto, Masao,Yamaguchi, Hideo
, p. 5027 - 5030 (2007/10/02)
A new general method for the synthesis of allyl ethers and allyl acetates is described.Allylmetal (group IVb) compounds, on treatment with thallium(III) salts in alcohols or acetic acid, gave the corresponding allyl ethers or allyl acetates in good yields.The reaction was successfully applied to the synthesis of the 6-membered cyclic ether 20 via the intramolecular, thallium(III)-mediated allylation reaction of the allylsilane 18.Keywords - allyl ether; allyl acetate; thallium(III) salt; allylsilane; allylstannane; intramolecular cyclization; umpolung