Stereochemistry and product distribution in the thiono-thiolo rearrangement of phosphorothioic esters. 4. Role of leaving-group solvation

K Bruzik, WJ Stec

Index: Bruzik, K.; Stec, W. Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1625 - 1630

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Citation Number: 10

Abstract

Results Influence of Reaction Medium Acidity on the Stereochemistry of the Rearrangement of 2-[(a-Methylbenzyl) oxy]-2-thiono-5, 5-dimethyl-1, 3, 2-dioxaphosphorinane (1). It has been shown that the rearrangement of 2-(2-butoxy)-(4), 2-[(a-deuteriobenzy1) oxyl-(5), and 2 4 (a-methylbenzyl) oxy]-2-thiono-5, 5-dimethyl-1, 3, 2-dioxaphosphorinane (1) in TFA- CH2C12 (1: lv/v) occurs with net inversion of configuration at the migrating carbon atom.' ...