Dioxolanylium Ions Derived from Carbohydrates. XI. Aminosugar Formation by trans Opening with the Trichloroacetimidoyl Neighbouring Group

S Jacobsen

Index: Jacobsen, Steffen Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1986 ,  vol. 40,  # 6  p. 498 - 504

Full Text: HTML

Citation Number: 1

Abstract

A variety of benzylidene sugars containing vicinal trichloroacetimidoyl groups have been oxidized by N-bromosuccinimide, to ascertain which structural features are necessary for neighbouring group participation from the iminoester in the opening of the transitory benzoxonium ion. The results indicate that the trichloroacetimidoyl group closely resembles the acyl group in its ability to participate, and that the resulting iminoester is strongly ...