The Journal of Organic Chemistry

Alkenes from base-promoted eliminations of. alpha.-halo sulfoximines

CR Johnson, HG Corkins

Index: Johnson,C.R.; Corkins,H.G. Journal of Organic Chemistry, 1978 , vol. 43, p. 4140 - 4143

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Citation Number: 6

Abstract

Upon treatment with base n-halo N-(p-tolylsulfony1) sulfoximines bearing a hydrogens undergo 1, 3 eliminations to yield alkenes in analogy to the Ramberg-Backlund reaction of a- halo sulfones. Treatment of benzylic ru-bromo Ai-(p-tolylsulfony1) sulfoximines with refluxing methanolic potassium hydroxide gave cis-alkenes as the major product, whereas under the same conditions a-chloro dialkylsulfoximines gave largely trans-alkenes. Neither NH nor ...