New Reactions of Alkylidenephosphoranes and their Preparative Uses III. Alkylidenephosphoranes and Reagents Containing Multiple Bonds


  • For Part I, see Angew. Chem. 77, 609 (1965) Angew. Chem. internat. Edit. 4, 583 (1965); for Part II, see Angew. Chem. 77, 651 (1965); Angew. Chem. internat. Edit. 4, 645 (1965).


A few examples of preparatively useful syntheses using alkylidenephosphoranes and substances containing a C[BOND]N or C[BOND]C double bond are the preparations of olefins, allenes, pyran derivatives, and cyclopropane derivatives. Olefins, ketones, and monocyclic compounds can be obtained by autoxidation of alkylidenephosphoranes; α, β-dioxo compounds (including cyclicones) can be prepared by oxidation with peroxy-acids. Alkylidenephosphoranes can also be used for the synthesis of azines and Schiff bases. Of the many possibilities offered by the Wittig reaction, only the preparation of tritiated aldehydes and olefins will be considered.