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Sigmatropic Rearrangements of Ylides Generated from N-(A-Cyano)benzyl-N,N-dimethyl-N-substituted Ammonium Salts with a Base

Zdrojewski T., Gołębiowski R., Mirkowska A., Jończyk A.

Polish Journal of Chemistry

1999

Vol. 73, nr 12

1955-1964

Quaternary ammonium salts 1-4, treated with four different base-solvent systems A-D, generated ylides YI and YII which in turn, rearranged with formation of the products 6,9 and/or 7,8 as the products of [1,2] or [2,3] shift, respectively. The products 9a,d eliminated dimethylamine, when refluexed in methanol to afford methy(Z)-B-cyanocinnamates 10a,d. The salts 2 and 4 generated ylides, which formed rearranged products in better yields than the salt 3.