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Note | Special issue | Vol 52, No. 1, 2000, pp.475-482
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S35
Reactions of α-Diazocycloalkanones with Thiocarbonyl Compounds

Bashkim Kelmendi, Grzegorz Mloston, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

Reactions of 2-diazocyclohexanone (7) with thioketones and a 1,3-thiazole-5(4H)-thione in THF at 50-60°C in the presence of 10% LiClO4 proceeded by elimination of N2 and yielded 4,5,6,7-tetrahydro-1,3-benzoxathiole derivatives (13-17). In the case of 2,2,4,4-tetramethylcyclobutane-1,3-dithione (12), a 1:5 mixture of cis- and trans- bisadduct (cis/trans-17) was obtained. Under analogous conditions, no reactions occurred with 5,5-dimethyl-2-diazo-cyclo-hexane-1,3-dione (18). Only in the presence of 2% Rh2(OAc)4, 18 reacted with dithione (12) yielding the 1,3-benzoxathiole derivative (19).