TY - JOUR
T1 - A Study of the Lithium in Ammonia Reduction of 3-Ethoxy cyclohexenone
AU - Watt, David S.
AU - McKenna, J. Michael
AU - Spencer, Thomas A.
PY - 1967
Y1 - 1967
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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U2 - 10.1021/jo01284a005
DO - 10.1021/jo01284a005
M3 - Article
AN - SCOPUS:1542637628
SN - 0022-3263
VL - 32
SP - 2674
EP - 2678
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -