Chemistry of diazocarbonyl compounds: XXVIII. Reaction of acyclic N-arylsulfonylacetamides with Rh(II)-carbenoids as a new synthetic route to alkyl acetimidoates |
| |
Authors: | A V Selivanova V V Nikolaev R R Kostikov V A Nikolaev J Siler B Schulze |
| |
Institution: | 1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia 2. Institut für Organische Chemie, Universit?t Leipzig, Johannisallee 29, Leipzig, 04103, Germany
|
| |
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. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|