Reactions of N-thioacetylmorpholine anion with iodoarenes and 1-iodoadamantane by the S RN1 mechanism

Abstract

The anion of N-acetylthiomorpholine 2 was studied in photostimulated reactions with iodobenzene 1a and 1-iodonaphthalene 1b in DMSO, giving good yields of the substitution products 3a and 3b by the S RN1 mechanism. The reaction of 1a with 2 is also induced with FeBr 2. 1-Iodoadamantane 4 did not react with the anion of N-acetylmorpholine, but reacted with 2 to give the substitution product 5 under irradiation. By competition experiments, acetophenone enolate ions are 1.4 times more reactive than 2 toward 1a and 3.3 times toward 4.