Azafulvenium methides: new extended dipolar systems

…, RC Storr, TL Gilchrist, P Rafferty

Index: Sutcliffe, Oliver B.; Storr, Richard C.; Gilchrist, Thomas L.; Rafferty, Paul Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 15 p. 1795 - 1806

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Citation Number: 32

Abstract

The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo [1, 2-c][1, 3] thiazole 2, 2-dioxide 20 (R= Me), 22 and 23 undergo sigmatropic [1, 8] H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo [1, 2-c][1, 3] oxazines 32. The analogous 1, 2-diazafulvenium methide 36 has been intercepted in [8π+ 2π] cycloadditions with electron-rich silylated acetylenes to give adducts 37–40. ...