Operationally simple and environmentally benign procedures have been developed to selectively reduce different α,β- unsaturated ketones, 4,4-dimethylcyclohex-2-ene-1-one (1), isophorone (2), benzylideneacetone (3), chalcone (4) by NaBH4 or by the system NaBH4 + CoCl2. Alternative reaction media to the extensively used MeOH have been explored and new procedures take advantage of the acceleration and chemoselectivity induced by water or by aqueous micellar solutions. It was possible to selectively and quantitatively afford pure products of 1,2 and of 1,4 reduction as well as the totally reduced compounds (yield and selectivity 90%) by simple changes in the experimental conditions.

Reduction of alfa, beta-Unsaturated Ketones by NaBH4 or NaBH4 + CoCl2: Selectivity Control by Water or by Aqueous Micellar Solutions

BRINCHI, Lucia;GERMANI, Raimondo;SAVELLI, Gianfranco
2000

Abstract

Operationally simple and environmentally benign procedures have been developed to selectively reduce different α,β- unsaturated ketones, 4,4-dimethylcyclohex-2-ene-1-one (1), isophorone (2), benzylideneacetone (3), chalcone (4) by NaBH4 or by the system NaBH4 + CoCl2. Alternative reaction media to the extensively used MeOH have been explored and new procedures take advantage of the acceleration and chemoselectivity induced by water or by aqueous micellar solutions. It was possible to selectively and quantitatively afford pure products of 1,2 and of 1,4 reduction as well as the totally reduced compounds (yield and selectivity 90%) by simple changes in the experimental conditions.
2000
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/162058
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