STEREOCHEMISTRY OF METHYLATION OF LITHIUM ENOLATES OF 2-METHYL-4-T-BUTYLCYCLOHEXANONE

被引：50

作者：

HUFF, BJL

TULLER, FN

CAINE, D

机构：

[1] School of Chemistry, Georgia Institute of Technology, Atlanta

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 10期

关键词：

D O I：

10.1021/jo01262a061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the lithium enolate of 4-t-butylcyclohexanone and the three lithium enolates derived from cis and trans-2-methyl-4-t-butylcyclohexanone with methyl iodide or methyl-d3 iodide in 1,2-dimethoxyethane has been investigated. In all cases, mixtures of stereoisomeric methylation products were obtained. The results have been interpreted by considering that the geometry of the transition state for the alkylation reaction closely resembles the reactants. © 1969, American Chemical Society. All rights reserved.

引用

页码：3070 / &

共 25 条

[1] CONFORMATIONAL ANALYSIS .51. CONFORMATIONS OF CYCLOHEXANONE RINGS IN SIMPLE MOLECULES [J].

ALLINGER, NL ;

BLATTER, HM ;

FREIBERG, LA ;

KARKOWSK.FM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (13) :2999-&

[2]

BHACCA MS, 1964, APPLICATIONS NMR SPE, P159

[3] ALKYLATION OF LITHIUM ENOLATES OF 2-METHYLCYCLOHEXANONE [J].

CAINE, D .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) :1868-&

[4]

CAINE D, 1966, TETRAHEDRON LETT, P4695

[5]

CAINE D, 1967, TETRAHEDRON LETT, P3399

[6]

CONIA JM, 1966, B SOC CHIM FR, P3881

[7]

CONIA JM, 1966, B SOC CHIM FR, P3888

[8]

CONIA JM, PERSONAL COMMUNICATI

[9]

GILMAN H, 1943, ORGANIC CHEMISTRY, V1, P486

[10]

HOUSE HO, 1963, J ORG CHEM, V28, P3362, DOI 10.1021/jo01047a022

← 1 2 3 →