The addition of organotin hydrides to isocyanates and isothiocyanates: synthesis and structure of some organotin-substituted amides

Abstract

Organotin hydrides add across the carbon---nitrogen double bond of aryl isocyanates (tin---nitrogen bond formation) and hexyl isocyanate (tin---carbon bond formation) and across the carbon---sulfur double bond of phenyl isothiocyanate (tin---sulfur bond formation) to afford in excellent yield 1:1 adducts. Structures have been assigned on the basis of IR and UV evidence.

Hexyl isocyanate (but not aryl isocyanates) and phenyl isothiocyanate are reduced to a small extent by triethyltin hydride to N-hexylformamide and N-phenylthioformamide.

Each of the adducts is readily hydrolyzed to the corresponding N-aryl(alkyl)-formamide or N-phenylthioformamide.