作者
Eric Block, Mohammad Aslam, Venkatachalam Eswarakrishnan, Kassu Gebreyes, John Hutchinson, Rajeshwari Iyer, Jean Alex Laffitte, Alan Wall
发表日期
1986/7
期刊
Journal of the American Chemical Society
卷号
108
期号
15
页码范围
4568-4580
出版商
American Chemical Society
简介
Haloalkanesulfonyl bromides including chloromethanesulfonyl bromide (1), bromomethanesulfonyl bromide (2),-bromoethanesulfonyl bromide (3), and iodomethanesulfonyl bromide (4) undergo free radical addition to olefins giving adducts which upon treatment with base afford dienes by a process termed the vinylogous Ramberg-Backlund reaction. In appropriate cases regioselectivity and/or stereoselectivity is observed in both the first addition step and in subsequent base-promoted elimination steps. Using this two-or three-step procedure, 1-alkenes are converted into 1, 3-alkadienes, 2-methyl-1-alkenes into 2-al-kyl-1, 3-butadienes, methylenecycloalkanes into 1-vinyl-1-cycloalkenes, cycloalkenes into 3-methylene-1-cycloalkenes, and 1-methylcycloalkenes into 1, 2-dimethylenecycloalkanes among other examples. Reagents 1-4 can also be used to convert trimethylsilyl enol ethers into-alkylidene ketones and …
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E Block, M Aslam, V Eswarakrishnan, K Gebreyes… - Journal of the American Chemical Society, 1986