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Azafulvenium methides: new extended dipolar systems

Sutcliffe, O.B. and Storr, R.C. and Gilchrist, T.L. and Rafferty, P. (2001) Azafulvenium methides: new extended dipolar systems. Journal of the Chemical Society, Perkin Transactions 1, 2001 (15). pp. 1759-1806. ISSN 1472-7781

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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 [8 + 2] cycloadditions with electron-rich silylated acetylenes to give adducts 37-40. This behaviour is partially explained by Frontier MO theory.