The efficiency of three azodicarboxylic acid derivatives and a stabili
zed phosphorane in the Mitsunobu type C-C bond formation was compared
utilizing the reactions of three nucleophiles of different pK(a)'s and
several alcohols of different structure types. The study established
the characteristics of each reagent. The synthesis of two insect phero
mone analogs was accomplished effectively using these homologation rea
ctions.