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Paper | Special issue | Vol 84, No. 2, 2012, pp.945-961
Published online, 29th August, 2011
DOI: 10.3987/COM-11-S(P)75
Reactivity of N-Alkylthiiranimines toward Simple Nucleophiles and Iso(thio)cyanates

Hildegard Nimmesgern, Ernst Schaumann,* and Gunadi Adiwidjaja

*Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

Hydrolysis of N-(1-dimethylcarbamoyl-1-methylethyl)-thiiranimines occurs with S-C(sp2) ring cleavage while attack of hydrochloric acid results in S-C(sp3) ring opening. The latter mode of ring opening is also observed in [3+2] cycloaddition reactions with iso(thio)cyanates where the heterocumulene reacts via the C-chalcogen bond; only a sterically less hindered isopropyl substituted thiiranimine adds to the C=N bond in isocyanates to yield 4-thiohydantoins. The cycloadducts give a variety of hydrolysis products, in particular imidazo[2,1-b]oxazoles and –thiazoles, oxazolones, and stable thietes. Insertion of a thiocarbonyl into an isopropyl CH bond is observed yielding an annulated cyclopropane unit.