When ethyl or phenyl azidoformate, or p-tolylsulphonyl azide are decomposed in warm tetrachlorothiophene, tetrachlorothiophene S,N-ylides are formed; 2,5-dichloro-, 2,5-dibromo-, and tetrabromo-thiophene on the other hand give products arising from attack at the α-position followed by rearrangement.
O. Meth-Cohn and G. van Vuuren, J. Chem. Soc., Chem. Commun., 1984, 190 DOI: 10.1039/C39840000190
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