Reductive Cleavage of N-Substituted 2-Aryl- l,3-oxazolidines: Generation of alfa-Amino-Substituted Carbanions
Academic Article
Publication Date:
1993
Short description:
Reductive Cleavage of N-Substituted 2-Aryl- l,3-oxazolidines:
Generation of alfa-Amino-Substituted Carbanions / Azzena, U.G., Giovanni, M., Cristina, N.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - (1993), pp. 6707-6711. [10.1021/jo00076a033]
abstract:
The behavior of several N-substibuted 2-aryl-1,3-oxazolidines has been investigated under conditions
of electron transfer from alkali metals in aprotic solvents. The reduction led to the regioselective
cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted
benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with
the aid of labeling experiments, showed the intermediate formation of a-tertiary amino-substituted
carbanions.
of electron transfer from alkali metals in aprotic solvents. The reduction led to the regioselective
cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted
benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with
the aid of labeling experiments, showed the intermediate formation of a-tertiary amino-substituted
carbanions.
Iris type:
1.1 Articolo in rivista
Keywords:
2-Aryl- l,3-oxazolidines; electron transfer; reductive cleavage
List of contributors:
Azzena, Ugo Gavino; Giovanni, Melloni; Cristina, Nigra
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