Syn elimination of alkyl selenoxides. Side reactions involving selenenic acids. Structural and solvent effects of rates

HJ Reich, S Wollowitz, JE Trend, F Chow…

Index: Reich,H.J. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 1697 - 1705

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Citation Number: 191

Abstract

The olefin-forming syn elimination of alkyl aryl selenoxides was examined. The formation of@-hydroxy selenides by addition of the elements of benzeneselenenic acid (PhSeOH) to olefin product was found to be a persistent side reaction unless an alkylamine was present during syn elimination. The selenium (I1) electrophile is provided by a comproportionation (reverse disproportionation) of PhzSez and PhSeOzH. If an intramolecular reaction is ...

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