SYNTHESIS AND ABSOLUTE CONFIGURATIONS OF SOME OPTICALLY ACTIVE CIS-AND TRANS-1,2-DISUBSTITUTED CYCLOPROPANES

被引：53

作者：

BERGMAN, RG

机构：

[1] Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 26期

关键词：

D O I：

10.1021/ja01054a032

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A number of cis- and trans-1,2-disubstituted cyclopropanes have been synthesized in both racemic and optically active form. Their maximum rotations and absolute configurations have been determined by chemical correlation with trans-2-methylcyclopropanecarboxylic acid (6). Application of Brewster´s rules of conformational asymmetry to the compounds prepared indicates that the theory is much more satisfactory when used to predict the rotations of trans- rather than cis-1,2-disubstituted cyclopropanes. © 1969, American Chemical Society. All rights reserved.

引用

收藏

页码：7405 / &

相关论文

共 30 条

[1] THE STEREOCHEMISTRY OF THE HUNSDIECKER REACTION ON A CYCLOPROPANE RING [J].

APPLEQUIST, DE ;

PETERSON, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (09) :2372-2376

[2] KINETIC ISOTOPE EFFECTS IN PYROLYSIS OF CYCLOPROPANE AND CYCLOBUTANE [J].

BENSON, SW ;

NANGIA, PS .

JOURNAL OF CHEMICAL PHYSICS, 1963, 38 (01) :18-&

[3]

BERGMAN RB, 1969, J AM CHEM SOC, V90, P7411

[4]

Brewster, 1967, TOP STEREOCHEM, P1, DOI [10.1002/9780470147115.ch1, DOI 10.1002/9780470147115.CH1]

[5] A USEFUL MODEL OF OPTICAL ACTIVITY .1. OPEN CHAIN COMPOUNDS [J].

BREWSTER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5475-5483

[6] A USEFUL MODEL OF OPTICAL ACTIVITY .3. THE OPTICAL ACTIVITY OF ENDOCYCLIC OLEFINS [J].

BREWSTER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5493-5500

[7] A USEFUL MODEL OF OPTICAL ACTIVITY .2. THE OPTICAL ACTIVITY OF SATURATED CYCLIC COMPOUNDS [J].

BREWSTER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5483-5493

[8] OPTICAL ISOMERIZATION DURING PYROLYSIS OF ALKYLCYCLOPROPANES . EVIDENCE FOR DIRADICAL INTERMEDIATES AND AN ESTIMATE OF THEIR RELATIVE RATES OF BOND ROTATION AND RING CLOSURE [J].

CARTER, WL ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (26) :7344-&

[9] Kinetics of the thermal isomerization of cyclopropane [J].

Chambers, TS ;

Kistiakowsky, GB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :399-405

[10] EXPERIMENTS DIRECTED TOWARD TOTAL SYNTHESIS OF TERPENES .7. SYNTHESIS OF (+-) -8BETA-CARBOMETHOXY-13-OXOPODOCARPANONE A DEGRADATION PRODUCT OF PHYLLOCLADENE [J].

CHURCH, RF ;

IRELAND, RE ;

MARSHALL, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (08) :2526-+