The transient 8π 1,7-dipolar azafulvenium methides 5 and 8 undergo sigmatropic [1,8] H shifts and the acyl derivatives 12 electrocyclise to give novel pyrrolooxazines 13; the related diazafulvenium methide 15 can be intercepted in 8π + 2π cycloadditions with silylated acetylenes.
Azafulvenium methides: new extended dipolar systems
O. B. Sutcliffe, R. C. Storr, T. L. Gilchrist, P. Rafferty and A. P. A. Crew, Chem. Commun., 2000, 675 DOI: 10.1039/B001521K
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