The Journal of Organic Chemistry

Alkylation of enolates from. beta.-dicarbonyl compounds with sulfonium salt electrophiles

ME Garst, BJ McBride

Index: Garst, Michael E.; McBride, Bill J. Journal of Organic Chemistry, 1983 , vol. 48, # 8 p. 1362 - 1364

Full Text: HTML

Citation Number: 11

Abstract

Eliel'l observed for the methyl analogues of 6 and 30, ring opening predominates in five- membered rings and dealkylation in six-membered rings. The dealkylation reaction using 1, 4-thioxane as the alkyl carrier should permit the ready transfer of any primary alkyl group. To promote ring opening in six-membered rings, the desired SN2 reaction was enhanced by making it an allylic displacement as in 8. The geometrical requirements for this process ...