Reaction of 2-tert-butoxy-4,5-benzo-1,3,2-dioxaphospholane with tribromoacetaldehyde

Abstract

The reaction of 2-tert-butoxy-4,5-benzo-1,3,2-dioxaphospholane with tribromo-acetaldehyde proceeds by initial halophilic attack on the bromine atom, leading to a product with retention of the P-Br bond (pyrocatechol bromophosphate) and an anion exchange product (pyrocatechol dibromovinylphosphate), and by initial attack at the carbon atom of the C=O group, which is accompanied by the elimination of isobutylene to form an α-hydroxyphosphonate. © 1990 Plenum Publishing Corporation.