Unprecedented iridium catalysed group transfer reactions of 1,3-thiazanes

Abstract

Intramolecular allyl, benzyl or methylene ester transfer is observed upon treatment of suitably functionalized 1,3-thiazanes with catalytic amounts of either anhydrous iridium trichloride or chlorotricarbonyliridium in benzene under a carbon monoxide atmosphere (e.g. N-allyl-2-phenyl-1,3-thiazane is converted to N,S-diallyl-N-benzyl-1,3-aminothiol; the allyl unit is provided by a second molecule of the thiazane, which is in turn converted into the corresponding thiazine by formal loss of propene).