280-33-1Relevant articles and documents
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Grob,C.A.,Hostynek,J.
, p. 1676 - 1686 (1963)
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A Product Study of 1-Adamantyl and 1-Bicyclooctyl Radicals in Hydrocarbon Solvents. An Unusually Large Hydrogen Isotope Effect
Engel, Paul S.,Chae, Woo-Ki,Baughman, Sharon A.,Marschke, Gregor E.,Lewis, Edward S.,et al.
, p. 5030 - 5034 (1983)
1-Adamantyl (ada.) and 1-bicyclooctyl (bo.) radicals have been generated by photolysis of the corresponding azoalkanes in various hydrocarbon solvents.Both radicals abstract hydrogen readily from hydrocarbons and they add to aromatic rings much faster than tert-butyl. does.Despite its reactivity, ada. is remarkably selective in hydrogen atom abstraction, preferring a benzylic hydrogen 25:1 over a cyclohexane hydrogen.The effect of solvent viscosity indicates that formation of the radical dimers biada and bibo occurs in the solvent cage.The most striking result of this work is a deuterium isotope effect of 25 for hydrogen transfer from cyclohexane to ada. at 65 deg C.Steric compression in the transition state is postulated to cause an unusually large tunnel correction and hence a large kH/kD.
A simple and straightforward approach toward selective C=C bond reduction by hydrazine
Chen, Hao,Wang, Jianmin,Hong, Xuechuan,Zhou, Hai-Bing,Dong, Chune
supporting information, p. 758 - 761 (2012/11/07)
A simple and straightforward method for reducing the C=C double bond with hydrazine is described. A number of representative C=C bonds in various steric and electronic environments were examined. Substituted alkenes can be selectively reduced in EtOH in the presence of hydrazine to give the corresponding products in up to 100% yields.
Cobalt-catalyzed reductive allylation of alkyl halides with allylic acetates or carbonates
Qian, Xin,Auffrant, Audrey,Felouat, Abdellah,Gosmini, Corinne
supporting information; experimental part, p. 10402 - 10405 (2011/12/03)
An efficient method for the direct allylation of alkyl halides catalyzed by simple cobalt(II) bromide has been developed. This reaction, using a variety of substituted allylic acetates or carbonates, provides the linear product as the major product. It displays broad substrate scope and good functional group tolerance. Copyright