While conformationally favourable thiocarbamates bearing an aromatic methoxy group undergo intramolecular ipso-substitution of the methoxy group by treatment with tris(trimethylsilyl)silane (TTMSS) and AIBN, either conformationally flexible or favourable ketones easily cyclise into a five- or six-membered rings by treatment with SmI2.
Unusual radical ipso-substitution reaction of an aromatic methoxy group induced by tris(trimethylsilyl)silane-AIBN or SmI2
T. Tanaka, R. Wakayama, S. Maeda, H. Mikamiyama, N. Maezaki and H. Ohno, Chem. Commun., 2000, 1287 DOI: 10.1039/B003742G
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