PREPARATION OF N,N-BIS(TRIMETHYLSILYL)-1-ALKENESULFENAMIDES AND THEIRDESILYLATIVE CONVERSION TO 1-ALKENESULFENIMINES - NEW STABLE 1-ALKENESULFENIC ACID-DERIVATIVES

Eight stable N,N-bis(trimethylsilyl)-1-alkenesulfenamides (3) were syn thesized by the reaction of 1-alkenesulfenate anions with TMSCl and Li HMDS. Compounds 3 were isolated either by distillation or by chromatog raphy 1-Alkenesulfenamides (3) can be desilylated in the presence of a ldehydes and ketones that do not bear alpha-hydrogens, to afford 1-alk enesulfenimines (7) either as single isomers or as mixtures of geometr ic isomers about the C=N bond. Protodesilylation of compounds 3 leads to 1-alkenesulfenamides (8) that have only hydrogens on the nitrogen. The parent 1-alkenesulfenamides 8 are not particularly stable, but cou ld be characterized. (C) 1996 Elsevier Science Ltd