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

MC Murguía, RA Rossi

Index: Murguia, Marcelo C.; Rossi, Roberto A. Tetrahedron Letters, 1997 , vol. 38, # 8 p. 1355 - 1358

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Citation Number: 30

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 SRN1 mechanism. The reaction of 1a with 2 is also induced with FeBr2. 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, ...