1, 4-Dioxaspiro [2.2] pentanes. Synthesis, spectroscopic properties, and reactions with nucleophiles

JK Crandall, DJ Batal, DP Sebesta…

Index: Crandall, Jack K.; Batal, David J.; Sebesta, David P.; Lin, Feng Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1153 - 1166

Full Text: HTML

Citation Number: 53

Abstract

A number of simple allenes have been converted cleanly to the corresponding 1, 4- dioxaspiro [2.2 lpentanes in good yields by oxidation with dimethyldioxirane. Mono-and trisubstituted allenes give the anti diastereomers with good stereoselectivity, whereas 1, 3- disubstituted allenes show only a slight preference for the anti, anti isomers, unless steric effects are extreme. Stereochemical assignments are based on steric considerations and ...