Abstract
Abstract Trimethylsilylmethyl isothiocyanate, bis(trimethylsilyl)methyl isothiocyanate, and tris(trimethylsilyl)methyl isothiocyanate were prepared. The fluoride-catalyzed reaction of trimethylsilylmethyl isothiocyanate with aldehydes or ketones afforded oxazolidine-2-thione derivatives, which involves the isothiocyanato carbanion as an intermediate. Imidazolidine-2-thiones were similarly prepared from imines. The reaction of bis(trimethylsilyl)methyl isothiocyanate with benzaldehyde in the presence of a catalytic amount of n-Bu4NF gave styryl isothiocyanate and 5-phenyl-4-trimethylsilyloxazolidine-2-thione. On the similar treatment of tris(trimethylsilyl)methyl isothiocyanate, 4-benzyl-5-phenyl-4-oxazoline-2-thione, and α-(trimethylsilyl)styryl isothiocyanate were obtained.
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