4-Nitro-3-thienyl phenyl sulphone (3) reacts with various sodium arenethiolates in methanol to give 5-arylthio-3-thienyl phenyl sulphones (4)(main products) and 2-arylthio-4-nitrothiophens (2). An anomalous addition–elimination mechanism is suggested to account for the formation of the cine-substitution products (2) and (4).
M. Novi, G. Guanti, C. Dell'Erba and D. Spinelli, J. Chem. Soc., Perkin Trans. 1, 1976, 2264 DOI: 10.1039/P19760002264
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