Tetrahedron letters

Thiones as superdipolarophiles

R Huisgen, E Langhals

Index: Huisgen, Rolf; Langhals, Elke Tetrahedron Letters, 1989 , vol. 30, # 39 p. 5369 - 5372

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Citation Number: 53

Abstract

Abstract According to kinetic measurements, the 1, 3-cycloadditions of diphenyldiazomethane to thioketones are much faster than those to α, β-unsaturated carbonyl compounds and nitriles previously regarded as record dipolarophiles. The primary cycloadducts are tetrasubstituted 1, 3, 4-thiadiazolines which extrude N 2 and furnish thiiranes via thiocarbonyl ylides.