Abstract
Alkyloxy- and alkylthiomethyleneiminium salts were derived from dimethylformamide (DMF) or N, N, N', N'-tetramethylurea (TMU). The reaction of each iminium salt with methanol gave methoxymethyleneiminium salts. The reaction of benzyloxymethyleneiminium salts (2) with hydrogen chloride, thiophenol, and aniline in the presence of pyridine gave benzylchloride, benzylphenylsulfide, and N-benzylaniline, respectively. The reaction of sodium benzyloxide with (8) and (10) gave dibenzyl ether and benzyl methyl sulfide, respectively. The iminium salts (12) derived from TMU was used for the esterification of sterically hindered alcohols and carboxylic acids.
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