The Journal of Organic Chemistry

Stereochemistry of amine additions to acetylenic and allenic sulfones and sulfoxides

WE Truce, LD Markley

Index: Truce,W.E.; Markley,L.D. Journal of Organic Chemistry, 1970 , vol. 35, # 10 p. 3275 - 3281

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Citation Number: 44

Abstract

That the 2, 3 adduct (2) does not arise by isomerization of the 1, 2 adduct (1) was shown by treating the pure nonconjugated ethylenimine adducts with ethylenimine in both ethanol and benzene; the starting adducts 1 were recovered unchanged. Resistance of adducts 1 to isomerization under reaction conditions rules out an allenic intermediate in the addition of ethylenimine to nonterminal acetylenic sulfones and sulfoxides, which yield only ...