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Communication | Special issue | Vol 5, No. 1, 1976, pp.141-146
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0141
■ 1,3-Dipolar Cycloadditions of Carbonyl Ylides to Thiocarbonyl and Carbonyl Compounds

Rolf Huisgen* and Scarlett Sustmann

*Institut für Organische Chemie, Universität München, Karlstrasse 23, D-80333 München, Germany

Abstract

α,β-Dicyanostilbene oxide at 120° undergoes electrocyclic ring opening to a carbonyl ylidc which can be trapped by cycloaddition to the CS double bond of O-methyl thiobenzoate, methyl dithiobenzoate and dimethyl trithiocarbonate to produce 1,3-oxathiolanes. The carbonyl ylide combines with diethyl mesoxalate to give a 1,3-dioxolane. The corresponding carbonyl ylide from α-cyanostilbene oxide affords a 1,3-dioxolane which suffers cycloreversion and renewed cycloadditon to give 2-phenyl-1,3-dioxolane-4,4,5,5-tetracarboxylic ester.