Carbohydrate research

Kinetic cyclohexylidenation and isopropylidenation of aldose diethyl dithioacetals

TB Grindley, CJP Cote, C Wickramage

Index: Grindley, T. Bruce; Cote, Christian J. P.; Wickramage, Chandra Carbohydrate Research, 1985 , vol. 140, p. 215 - 238

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Citation Number: 31

Abstract

Abstract Aldose diethyl dithioacetals react with 1.2 equivalents of 1-ethoxycyclohexene or 2- methoxypropene in N, N-dimethylformamide at 0 with p-toluenesulfonic acid as catalyst to give the five-membered ring acetal attached to the two terminal oxygen atoms as the major product in every case. In most instances, a small proportion of the terminal, six-membered ring acetal was also obtained, and in a few cases, terminal seven-membered ring acetals ...