Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates View Full Text


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Article Info

DATE

2006-12

AUTHORS

A. V. Selivanova, V. V. Nikolaev, R. R. Kostikov, V. A. Nikolaev, J. Siler, B. Schulze

ABSTRACT

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. More... »

PAGES

1792-1799

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428006120074

DOI

http://dx.doi.org/10.1134/s1070428006120074

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1015138927


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