Thiones as superdipolarophiles. Rates and equilibria of nitrone cycloadditions to thioketones

…, L Fisera, H Giera, R Sustmann

Index: Huisgen, Rolf; Fisera, Lubor; Giera, Henry; Sustmann, Reiner Journal of the American Chemical Society, 1995 , vol. 117, # 38 p. 9671 - 9678

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Citation Number: 75

Abstract

Abstract: 1, 3-Dipolar cycloadditions of N-methyl-C, C-diphenylnitrone (15) and N-methyl-C- phenylnitrone (16) with aliphatic thioketones are equilibrium reactions. The 1, 4, 2- 0xathiazolidines were characterized and their dissociation constants measured by'H NMR analysis and by visible spectrophotometry. of the adduct 28 from 16 and 2, 2, 6, 6- tetramethylcyclohexanethione (27) was determined from 20-76" C, revealing &&d=-10.8 ...