960161-55-1Relevant articles and documents
Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates
Selivanova,Nikolaev,Kostikov,Nikolaev,Siler,Schulze
, p. 1792 - 1799 (2007/10/03)
A new procedure was proposed for the synthesis of alkyl acetimidoates via alkylation of the carbonyl group in N-arylsulfonylacetamides with Rh(II)-carbenoids. The procedure ensures preparation in good yield of acetimidoates having a polyfunctionalized O-alkyl group. The obtained alkyl acetimidoates in crystal exist as E isomers with respect to the C=N bond and as s-cis conformers relative to the C-OCHRR' bond. Alkyl N- arylsulfonylacetimidoates react with ammonia and hydrazine hydrate to give in good yield the corresponding carboximidamides(hydrazides) via replacement of the O-alkyl group. Unlike structurally related compounds having simple alkyl or aryl groups on the nitrogen atom, N-arylsulfonylacetimidoates readily undergo hydrolysis in the presence of moisture and traces of acids.