Two-Step Method for the Transformation of 3-Phospholene Oxides to 1,4-Dihydro-1,4-Azaphosphorine Oxides.

摘要

We recently showed that 3-phospholene 1-oxides may be conveniently converted to bis(beta-oxoalkyl) phosphine oxides by oxonolysis at - 78 degrees C, followed by reduction of the ozonide with trimethyl phosphite. These carbonyl compounds are potentially of great value as synthetic intermediates, and it has already been shown that certain of them (R superscript 2 = H or CH3) can be cyclized by aldol condensation in a synthesis of the 1.6-dihydro-3(2H)-phosphorinone system. We have now coupled the synthesis of the bis(beta-oxoalkyl) compounds with the synthesis of 1,4-dihyldro-1,4-azaphosphorines, which in effect provides a two-step transformation of the readily available phospholene system to the azaphosphorine system. (Author)