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Paper | Regular issue | Vol 31, No. 1, 1990, pp.47-57
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5095
Chemistry of Silyl Thioketones. Part 6. Synthesis of 5-Membered Silyl-heterocycles via 1,3-Dipolar Cycloaddition to Aryl Silyl Thioketones

Bianca F. Bonini, Gaetano Maccagnani,* Germana Mazzanti, Ghamel Abdel-Lateef Achmed Atwa, Paolo Zani, and Gaetano Barbaro

*Dipartimento di Chimica Organica "A Mangini", Università degli Studi di Bologna, Viale Risorgimento, 4, I-40136 Bologna , Italy


Aryl silyl thioketones react with 1,3-dipoles (nitriloxides, nitrilimine and nitrile ylide) to give regiospecifically silyl thiaheterocycles. These cycloadducts undergo desilylation leading either to ring fragmentation products or to the H-substituted heterocycles.