The Journal of Organic Chemistry

Selenosulfonation of acetylenes: preparation of novel. beta.-(phenylseleno) vinyl sulfones and their conversion to acetylenic and. beta.-functionalized sulfones

TG Back, S Collins, RG Kerr

Index: Back, Thomas G.; Collins, Scott; Kerr, Russell G. Journal of Organic Chemistry, 1983 , vol. 48, # 18 p. 3077 - 3084

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Citation Number: 91

Abstract

4 of this work and include several new examples. In addition, we have found that adducts 3 are readily oxidized to selenoxides 4, which smoothly undergo syn or base-catalyzed eliminations to afford acetylenic sulfones 5 (eq 3). Products 5 are of current interest as dienophiles in Diels-Alder cycloadditionsI6 as electrophiles in Michael additions,'and in other applications. 8 We also describe related reactions which permit the conversion of ...