Stereochemical control in Wittig olefin synthesis. Preparation of the pink bollworm sex pheromone mixture, gossyplure

RJ Anderson, CA Henrick

Index: Anderson,R.J.; Henrick,C.A. Journal of the American Chemical Society, 1975 , vol. 97, p. 4327 - 4334

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Citation Number: 104

Abstract

Abstract: Stereochemical control of the Wittig reaction of the primary aldehyde 6 with the nonstabilized alkylide, triphenylphosphonium n-pentylide 7, is achieved by controlled partial equilibration of the intermediate adducts. These conditions are applied to the direct synthesis of the mixture of insect sex pheromones," gossyplure", which is a 1! 1 mixture of (72, llZ)-and (7Z, llE)-7, ll-hexadecadien-l-yl acetate (la and 2a, respectively). The ...