. alpha.-Haloalkanesulfonyl bromides in organic synthesis. 5. Versatile reagents for the synthesis of conjugated polyenes, enones, and 1, 3-oxathiole 1, 1-dioxides

E Block, M Aslam, V Eswarakrishnan…

Index: Block,E.; Aslam,M.; Eswarakrishnan,V. Journal of the American Chemical Society, 1986 , vol. 108, p. 4568

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Citation Number: 84

Abstract

Abstract: a-Haloalkanesulfonyl bromides including chloromethanesulfony1 bromide (l), bromomethanesulfonyl bromide (2), a-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 ...