Thionium ions as carbonyl substitutes. Synthesis of cyclic imino thioethers and lactams

BM Trost, M Vaultier, ML Santiago

Index: Trost, Barry M.; Vaultier, Michel; Santiago, Maria L. Journal of the American Chemical Society, 1980 , vol. 102, # 27 p. 7929 - 7932

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Citation Number: 41

Abstract

IR band at 2100 f 10 cm-'and 13C peaks for the carbon bearing azide and the S-CH3 carbon at 6 71.7-80.8 and 10.2-12.6, respectively. While the azides appeared to be reasonably stable and were purified by normal chromatographic procedures, the pure azides were normally not stored for long times. Addition of 4 equiv of trifluoroacetic acid to a chloroform solution of the a-azido sulfide led to a rapid and virtually quantitative rearrangement ...