A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone

David S. Watt; J. Michael McKenna; Thomas A. Spencer

doi:10.1021/jo01284a005

A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone

David S. Watt, J. Michael McKenna, Thomas A. Spencer

Molecular and Cellular Biochemistry

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Abstract

The composition of the product mixture from the reduction of 3-ethoxycyclohexenone (1) by lithium in ammonia under a variety of conditions has been determined. By appropriate choice of conditions, the predominant product can be made any of four compounds: cyclohexanone (2), cyclohexanol (3), 3-ethoxycyclohexanone (4), or cis-3-ethoxycyclohexanol (5). At -78°, products formed via elimination of ethoxide from enolate anion 9, viz., 2 and 3, are not observed. At -33° this elimination has t_1/2, of ca. 7 min. Use at either temperature of absolute ethanol as a quenching reagent rather than ammonium chloride favors formation of the hydroxylic products 3 and 5.

Original language	English
Pages (from-to)	2674-2678
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	32
Issue number	9
DOIs	https://doi.org/10.1021/jo01284a005
State	Published - 1967

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Organic Chemistry

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title = "A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone",

abstract = "The composition of the product mixture from the reduction of 3-ethoxycyclohexenone (1) by lithium in ammonia under a variety of conditions has been determined. By appropriate choice of conditions, the predominant product can be made any of four compounds: cyclohexanone (2), cyclohexanol (3), 3-ethoxycyclohexanone (4), or cis-3-ethoxycyclohexanol (5). At -78°, products formed via elimination of ethoxide from enolate anion 9, viz., 2 and 3, are not observed. At -33° this elimination has t1/2, of ca. 7 min. Use at either temperature of absolute ethanol as a quenching reagent rather than ammonium chloride favors formation of the hydroxylic products 3 and 5.",

author = "Watt, {David S.} and McKenna, {J. Michael} and Spencer, {Thomas A.}",

year = "1967",

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T1 - A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone

AU - Watt, David S.

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AU - Spencer, Thomas A.

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N2 - The composition of the product mixture from the reduction of 3-ethoxycyclohexenone (1) by lithium in ammonia under a variety of conditions has been determined. By appropriate choice of conditions, the predominant product can be made any of four compounds: cyclohexanone (2), cyclohexanol (3), 3-ethoxycyclohexanone (4), or cis-3-ethoxycyclohexanol (5). At -78°, products formed via elimination of ethoxide from enolate anion 9, viz., 2 and 3, are not observed. At -33° this elimination has t1/2, of ca. 7 min. Use at either temperature of absolute ethanol as a quenching reagent rather than ammonium chloride favors formation of the hydroxylic products 3 and 5.

AB - The composition of the product mixture from the reduction of 3-ethoxycyclohexenone (1) by lithium in ammonia under a variety of conditions has been determined. By appropriate choice of conditions, the predominant product can be made any of four compounds: cyclohexanone (2), cyclohexanol (3), 3-ethoxycyclohexanone (4), or cis-3-ethoxycyclohexanol (5). At -78°, products formed via elimination of ethoxide from enolate anion 9, viz., 2 and 3, are not observed. At -33° this elimination has t1/2, of ca. 7 min. Use at either temperature of absolute ethanol as a quenching reagent rather than ammonium chloride favors formation of the hydroxylic products 3 and 5.

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A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone

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