The Mitsunobu reaction of tetrachlorophthalimide

Tetrachlorophthalimide is shown to be an excellent agent for Mitsunobu disp lacement of primary hydroxyl groups in a wide variety of substrates. Second ary alcohols also react readily, except in carbohydrate derivatives where t here is a low rate of success. In a competition experiment between phthalim ide and its tetrachloro counterpart, there was no trace of a product from t he former.