On irradiation in acetonitrile, the 3-azido-2-vinylthiophenes (4) give the thieno[3,2-b]pyrroles (8) as the sole, or major, products formed by migration of the group Y (Scheme 2) in preference to or in competition with the group Z in the non-aromatic fused 2H-pyrrole intermediate (5), sulphur groups (Y = PhS, MeS, PhSO, PhSO2, MeSO, MeSO2) migrating particularly rapidly.
R. S. Gairns, C. J. Moody and C. W. Rees, J. Chem. Soc., Chem. Commun., 1985, 1818 DOI: 10.1039/C39850001818
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