Organometallic reactions. Part XIX. Some reactions of aldehydes with aminotin compounds

Abstract

N-Phenylhexabutyldistannazare reacts with acetaldehyde to give bistributylin oxide and ethylideneaniline. A similar reaction occurs between chloral and N-ethyl distannazanes to give 2,2,2-trichloroethylideneethylamine and the corresponding distannoxane. With N-aryl hexabutyldistannazanes, however, the reaction of chloral is more complicated; initially a 2 : 1 chloral–distannazane adduct is formed, and the decomposition products now include tributyltrichloromethyltin and the N-tributylstannylformarylamide.

Protolysis of the arylexabutyldistannazanes gives the N-tributylstannylarylamines; these new react with chloral to give stable adducts, the 1,1,1-trichloro-2-arylamino-2-tributylstannyloxyethanes, which can also be obtained by the azeotropic dehydration of a mixture of bistributyltin oxide and the parent aminohydroxytrichloroethane. Azeotropic dehydration of the aminohydroxytrichloroethanes in the absence of an organotin compound gives the 2,2,2-trichloroethylidene arylamines, which do not take part in addition reactions with triorganotin oxygen and nitrogen compounds.