One-Pot Synthesis of N-((Trimethylsilyl)methyl)imines and (Trimethylsilyl)methyl-Substituted Heterocumulenes from (Trimethylsilyl)methyl Azide

Article abstract of DOI:10.1021/jo00189a006

The reactions of ((trimethylsilyl)methyl)iminotriphenylphosphorane, prepared in situ from (trimethylsilyl)methyl azide and triphenylphosphine, with carbonyl compounds and with heterocumulenes such as carbon dioxide, carbon disulfide, isocyanates, isothiocyanates, and a ketene provide convenient one-pot syntheses of the corresponding N-((trimethylsilyl)methyl)imines and (trimethylsilyl)methyl-substituted heterocumulenes, which are versatile reagents for the synthesis of heterocyclic compounds.