REACTIONS OF N-THIOACETYLMORPHOLINE ANION WITH IODOARENES AND 1-IODOADAMANTANE BY THE S(RN)1 MECHANISM

The anion of N-acetylthiomorpholine 2 was studied in photostimulated r eactions with iodobenzene 1a and 1-iodonaphthalene Ib in DMSO, giving good yields of the substitution products 3a and 3b by the S(RN)1 mecha nism. The reaction of 1a with 2 is also induced with FeBr2. 1-Iodoadam antane 4 did not react with the anion of N-acetylmorpholine, but react ed with 2 to give the substitution product 5 under irradiation. By com petition experiments, acetophenone enolate ions are 1.4 times more rea ctive than 2 toward la and 3.3 times toward 4. (C) 1997 Elsevier Scien ce Ltd.