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Cyclisations Homolytiques Sur Un Carbonyle: Reexamen Des Reductions Des γ-Chlorobutyrophenone et Chloro-6 Hexanal Par L'hydrure de Tributyletain by Bernard Maillard; Christian Gardrat; Marie-Josephe Bourgeois is a Chemistry article available to read on EtoBox.

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Determination of the reactivity of Bu$n' with the carbonyl group of an alkyl aryl ketone and the chlorine atom of a primary alkyl chloride have shown similar types of reaction. These results led us to reconsider the mechanism of 2-phenyltetrahydrofuran formation in reduction reactions of y-chlorobutyrophenone by tributyltin hydride. This cyclic ether was obtained by elimination of tributyltin chloride from the product of carbonyl hydrostannation. A similar study on an aldehyde and a l-chloroalkane revealed the mechanism of cyclohexanol formation in reduction reactions of 6-chlorohexanal by tributyltin hydride. Tributyltin hydride treatment of 7-chloroheptan2-one and 6-chlorohexan-2-one led to heptan-2-one and hexan-2-one in good yields; no cyclization product is observed. La determination des reactivites relatives de Bu,Sn' envers l'addition 5 un carbonyle d'une alkylarylcetone et l'arrachement d'un atome de chlore a un chloro-1 alcane nous a amen& a reconsiderer le mecanisme de formation du phenyl-2 tetrahydrofuranne lors de la reduction de la y-chlorobutyrophenone par l'hydrure de tributyletain. L'heterocycle est obtenu par elimination de chlorure de tributyletain a partir du com

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Author

Bernard Maillard; Christian Gardrat; Marie-Josephe Bourgeois

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

1982

Language

FR

Field

Chemistry (Physical Sciences)