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SYNTHESIS AND ABSOLUTE CONFIGURATIONS OF SOME OPTICALLY ACTIVE CIS-AND TRANS-1,2-DISUBSTITUTED CYCLOPROPANES
被引:52
作者
:
BERGMAN, RG
论文数:
0
引用数:
0
h-index:
0
机构:
Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena
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
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[1]
THE STEREOCHEMISTRY OF THE HUNSDIECKER REACTION ON A CYCLOPROPANE RING
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[J].
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KINETIC ISOTOPE EFFECTS IN PYROLYSIS OF CYCLOPROPANE AND CYCLOBUTANE
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[J].
JOURNAL OF CHEMICAL PHYSICS,
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: 18
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[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]
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A USEFUL MODEL OF OPTICAL ACTIVITY .1. OPEN CHAIN COMPOUNDS
BREWSTER, JH
论文数:
0
引用数:
0
h-index:
0
BREWSTER, JH
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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81
(20)
: 5475
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[6]
A USEFUL MODEL OF OPTICAL ACTIVITY .3. THE OPTICAL ACTIVITY OF ENDOCYCLIC OLEFINS
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[J].
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: 5493
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[J].
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OPTICAL ISOMERIZATION DURING PYROLYSIS OF ALKYLCYCLOPROPANES . EVIDENCE FOR DIRADICAL INTERMEDIATES AND AN ESTIMATE OF THEIR RELATIVE RATES OF BOND ROTATION AND RING CLOSURE
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[9]
Kinetics of the thermal isomerization of cyclopropane
Chambers, TS
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Harvard Univ, Chem Lab, Cambridge, MA USA
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EXPERIMENTS DIRECTED TOWARD TOTAL SYNTHESIS OF TERPENES .7. SYNTHESIS OF (+-) -8BETA-CARBOMETHOXY-13-OXOPODOCARPANONE A DEGRADATION PRODUCT OF PHYLLOCLADENE
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→
共 30 条
[1]
THE STEREOCHEMISTRY OF THE HUNSDIECKER REACTION ON A CYCLOPROPANE RING
APPLEQUIST, DE
论文数:
0
引用数:
0
h-index:
0
APPLEQUIST, DE
PETERSON, AH
论文数:
0
引用数:
0
h-index:
0
PETERSON, AH
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1960,
82
(09)
: 2372
-
2376
[2]
KINETIC ISOTOPE EFFECTS IN PYROLYSIS OF CYCLOPROPANE AND CYCLOBUTANE
BENSON, SW
论文数:
0
引用数:
0
h-index:
0
BENSON, SW
NANGIA, PS
论文数:
0
引用数:
0
h-index:
0
NANGIA, PS
[J].
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
BREWSTER, JH
论文数:
0
引用数:
0
h-index:
0
BREWSTER, JH
[J].
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
BREWSTER, JH
论文数:
0
引用数:
0
h-index:
0
BREWSTER, JH
[J].
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
BREWSTER, JH
论文数:
0
引用数:
0
h-index:
0
BREWSTER, JH
[J].
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
CARTER, WL
论文数:
0
引用数:
0
h-index:
0
CARTER, WL
BERGMAN, RG
论文数:
0
引用数:
0
h-index:
0
BERGMAN, RG
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1968,
90
(26)
: 7344
-
&
[9]
Kinetics of the thermal isomerization of cyclopropane
Chambers, TS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Chem Lab, Cambridge, MA USA
Harvard Univ, Chem Lab, Cambridge, MA USA
Chambers, TS
Kistiakowsky, GB
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Chem Lab, Cambridge, MA USA
Harvard Univ, Chem Lab, Cambridge, MA USA
Kistiakowsky, GB
[J].
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
CHURCH, RF
论文数:
0
引用数:
0
h-index:
0
CHURCH, RF
IRELAND, RE
论文数:
0
引用数:
0
h-index:
0
IRELAND, RE
MARSHALL, JA
论文数:
0
引用数:
0
h-index:
0
MARSHALL, JA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1966,
31
(08)
: 2526
-
+
←
1
2
3
→