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ELECTRONIC AND STERIC INFLUENCES ON FACE SELECTION DURING THE OXY-COPE REARRANGEMENT OF AN ALPHA-ALLYL-ALPHA-VINYLBENZYL ALCOHOL
被引:21
作者
:
LIN, MH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
LIN, MH
WATSON, WH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
WATSON, WH
KASHYAP, RP
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
KASHYAP, RP
LENOBLE, WJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
LENOBLE, WJ
机构
:
[1]
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
[2]
TEXAS CHRISTIAN UNIV,DEPT CHEM,FT WORTH,TX 76129
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
1990年
/ 55卷
/ 11期
关键词
:
D O I
:
10.1021/jo00298a041
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
The racemic RR, SS and RS, SR diastereomers of 5-(5-fluoroadamant-2-ylidene)-4-hydroxy-4-phenyl-l-pentene (1-F) have been synthesized. Their configurations have been determined by means of 13C NMR as well as by way of an X-ray diffraction study of the acetate of the former alcohol. Both alcohols undergo the oxy-Cope rearrangement to give mixtures of the (E) and (Z)-2-allyl-2-benzoyl-5-fluoroadamantanes (5-F). Analysis of these mixtures allows the conclusions to be drawn that the preferred site of the phenyl group in the chair transition states is the quasi-equatorial one, and that the electronically preferred face of the adamantyl terminus is that syn to the fluorine (zu face). These preferences amount to factors of 2.75 and 1.54, respectively. Hyperconjugation involving the incipient a orbital can account for the electronic preference observed. Pyramidalization of C2 in the acetate of 1-F was not detectible in the X-ray diffraction study. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:3597 / 3602
页数:6
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CHEMISTRY OF BRIDGED AROMATICS - A STUDY OF THE SUBSTITUENT EFFECT ON THE COURSE OF BOND-CLEAVAGE OF "9,10-DIHYDRO-9,10-ETHANOANTHRACENES AND AN OXYANION-ASSISTED RETRO-DIELS-ALDER REACTION
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THE ANIONIC OXY-COPE REARRANGEMENT - STRUCTURAL EFFECTS IN THE GAS-PHASE AND IN SOLUTION
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INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
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DEFINITIVE IDENTIFICATION OF THE C-5 AND C-7 NMR SIGNALS OF ADAMANTAN-2-OL
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0
引用数:
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h-index:
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SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
CHEUNG, CK
LENOBLE, WJ
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0
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0
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SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
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[J].
MAGNETIC RESONANCE IN CHEMISTRY,
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HYPERCONJUGATION AS A STEREOINDUCTIVE FACTOR IN THE APPROACH OF ELECTROPHILES TO TRIGONAL CARBON
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0
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SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
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SRIVASTAVA, S
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[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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NEIGHBORING CARBON AND HYDROGEN .11. SOLVOLYSIS OF EXO-NORBORNYL PARA-BROMOBENZENESULFONATE
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[J].
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ZOECKLER, MT
CARPENTER, BK
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引用数:
0
h-index:
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CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
CARPENTER, BK
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(25)
: 7661
-
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[39]
1986, PN2691040340 NIC INS
←
1
2
3
4
→
共 39 条
[31]
CHEMISTRY OF BRIDGED AROMATICS - A STUDY OF THE SUBSTITUENT EFFECT ON THE COURSE OF BOND-CLEAVAGE OF "9,10-DIHYDRO-9,10-ETHANOANTHRACENES AND AN OXYANION-ASSISTED RETRO-DIELS-ALDER REACTION
RAJANBABU, TV
论文数:
0
引用数:
0
h-index:
0
RAJANBABU, TV
EATON, DF
论文数:
0
引用数:
0
h-index:
0
EATON, DF
FUKUNAGA, T
论文数:
0
引用数:
0
h-index:
0
FUKUNAGA, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1983,
48
(05)
: 652
-
657
[32]
THE ANIONIC OXY-COPE REARRANGEMENT - STRUCTURAL EFFECTS IN THE GAS-PHASE AND IN SOLUTION
ROZEBOOM, MD
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
ROZEBOOM, MD
KIPLINGER, JP
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
KIPLINGER, JP
BARTMESS, JE
论文数:
0
引用数:
0
h-index:
0
机构:
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
BARTMESS, JE
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1984,
106
(04)
: 1025
-
1029
[33]
DIASTEREOMERIC TRANSITION-STATES - RELATIVE ENERGIES OF THE CHAIR AND BOAT REACTION PATHWAYS IN THE COPE REARRANGEMENT
SHEA, KJ
论文数:
0
引用数:
0
h-index:
0
SHEA, KJ
PHILLIPS, RB
论文数:
0
引用数:
0
h-index:
0
PHILLIPS, RB
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1980,
102
(09)
: 3156
-
3162
[34]
DEFINITIVE IDENTIFICATION OF THE C-5 AND C-7 NMR SIGNALS OF ADAMANTAN-2-OL
SRIVASTAVA, S
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SRIVASTAVA, S
CHEUNG, CK
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
CHEUNG, CK
LENOBLE, WJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
LENOBLE, WJ
[J].
MAGNETIC RESONANCE IN CHEMISTRY,
1985,
23
(04)
: 232
-
235
[35]
HYPERCONJUGATION AS A STEREOINDUCTIVE FACTOR IN THE APPROACH OF ELECTROPHILES TO TRIGONAL CARBON
SRIVASTAVA, S
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SRIVASTAVA, S
LENOBLE, WJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794
LENOBLE, WJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1987,
109
(19)
: 5874
-
5875
[36]
NEIGHBORING CARBON AND HYDROGEN .11. SOLVOLYSIS OF EXO-NORBORNYL PARA-BROMOBENZENESULFONATE
WINSTEIN, S
论文数:
0
引用数:
0
h-index:
0
WINSTEIN, S
TRIFAN, D
论文数:
0
引用数:
0
h-index:
0
TRIFAN, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1952,
74
(05)
: 1154
-
1160
[37]
NEIGHBORING CARBON AND HYDROGEN .10. SOLVOLYSIS OF ENDO-NORBORNYL ARYLSULFONATES
WINSTEIN, S
论文数:
0
引用数:
0
h-index:
0
WINSTEIN, S
TRIFAN, D
论文数:
0
引用数:
0
h-index:
0
TRIFAN, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1952,
74
(05)
: 1147
-
1154
[38]
STEREOCHEMISTRY OF AN ALKOXIDE-ACCELERATED [1,3] MIGRATION
ZOECKLER, MT
论文数:
0
引用数:
0
h-index:
0
机构:
CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
ZOECKLER, MT
CARPENTER, BK
论文数:
0
引用数:
0
h-index:
0
机构:
CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853
CARPENTER, BK
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(25)
: 7661
-
7663
[39]
1986, PN2691040340 NIC INS
←
1
2
3
4
→