'Phospha-variations' on the themes of Staudinger and Wittig: phosphorus analogs of Wittig reagents

The Wittig and Aza-Wittig reactions have undergone tremendous development over the past 50 years in light of their potential in organic synthesis to construct carbon-carbon and carbon -nitrogen double bonds. In contrast, the development of the analogous phospha-Wittig reaction has only seen progress over the last 12 years. A phospha-Wittig process is one that uses phosphaylides to convert carbonyl compounds to new materials possessing phosphorus-carbon double bonds (phosphaalkenes). The phospha-Wittig reaction has evolved from initial work involving metal-assisted phospha-Wittig reactions, to phospha-Wittig reactions of terminal phosphinidene complexes to, more recently, free phosphanylidene-sigma (4)-phosphoranes as phospha-Wittig reagents. The major developments in the phospha-Wittig reaction are highlighted and divided into these three methodologies. The complementary nature and the differences between the three approaches is also discussed. Finally, wherein applicable, comparisons between the Wittig reaction and the phospha-Wittig reaction are presented. (C) 2000 Elsevier Science B.V. All rights reserved.