The Synthesis of 3-Phosphabicyclo[3.1.0]- hexane 3-Oxides and 1,2-Dihydrophosphinine 1-Oxides with Lipophilic P-Alkoxy Substituents by Ring Enlargement

Abstract

A series of 1‐alkoxy‐3‐phospholene 1‐oxides available from the microwave‐assisted direct esterification of 1‐hydroxy‐3‐phospholene oxide was converted to the two diastereomers of 6,6‐dichloro‐3‐phosphabicyclo[3.1.0]hexane 3‐oxides by the addition of dichlorocarbene to the double bond. Thermolysis of the 3‐phospholene oxide–dichlorocarbene adducts afforded the corresponding 1,2‐dihydrophosphinine 1‐oxides as a ca. 3:1 mixture of two double bond isomers. Relative stability of the isomers of the intermediates and the products and their stereostructures were evaluated by B3LYP/6‐31G(d,p) calculations.

The Impact of Microwaves on Organophosphorus Chemistry

“…Sensitive esters were prepared in another way . The cyclic phosphinates were utilized in the synthesis of other derivatives ,…”