The Journal of Organic Chemistry

Reactivity of the thiazolium C2 ylide in aprotic solvents: novel experimental evidence for addition rather than insertion reactivity

YT Chen, F Jordan

Index: Chen, Yao-Tsung; Jordan, Frank Journal of Organic Chemistry, 1991 , vol. 56, # 17 p. 5029 - 5038

Full Text: HTML

Citation Number: 56

Abstract

Two thiazolium compounds were synthesized specifically labeled at their C2 positions: 3, 4, 5-trimethy1 [2-lsC] thiazOlium nitrate and 3-benzyl-b (B-ethoxyethyl)-4methyl [2-'gC] thiazoliu bromide, with a view to examine their pathways leading to dimerization in strongly basic medium using 19C NMR. On addition of less than 1 equiv of base the N-methyl ion fist formed an unsymmetrical dimer in which the C2 atom of two molecules were bonded to ...