PROTON NUCLEAR MAGNETIC RESONANCE ANALYSIS OF STABLE CLASSICAL 2-PHENYL-2-NORBORNYL AND RELATED CATIONS

被引：65
作者：
FARNUM, DG
MEHTA, G
机构：
[1] Department of Chemistry, Michigan State University, East Lansing
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 12期
关键词：
D O I：
10.1021/ja01040a028
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 100-Mc nmr spectrum of the 2-phenyl-2-norbornyl cation has been analyzed with the aid of deuterium labeling, spin decoupling, and computer simulation. From a comparison with several related norbornyl and bicyclo[2.2.2]octyl systems it is concluded that the title cation is classical. Some dramatic examples of the low-field chemical shifts of bridgehead norbornyl hydrogens are described. © 1969, American Chemical Society. All rights reserved.
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页码：3256 / &
相关论文
共 27 条
[1]  
BERSON JA, 1964, J AM CHEM SOC, V86, P609, DOI 10.1021/ja01058a015
[2]   RING EXPANSION ROUTE TO BICYCLIC CARBONIUM IONS .1. MULTIPLE REARRANGEMENT OF ENDO-2-NORBORNYLCARBINYL SYSTEM [J].
BERSON, JA ;
REYNOLDSWARNHOFF, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (04) :595-&
[3]  
BETHELL D, 1967, CARBONIUM IONS, P280
[4]  
BETHELL D, 1967, CARBONIUM IONS, P279
[5]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[6]   RATES OF SOLVOLYSIS OF RHO-NITROBENZOATES OF EXO-ENDO TERTIARY NORBORNEOLS . CRITICAL EXAMINATION OF EXO-ENDO RATE RATIO AS BASIS FOR POSTULATED NONCLASSICAL STRUCTURE OF NORBORNYL CATION [J].
BROWN, HC ;
CHLOUPEK, FJ ;
REI, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (06) :1248-+
[7]  
BROWN HC, 1968, J AM CHEM SOC, V90, P2693
[8]   ON NORBORNYL CATION PROBLEM [J].
COREY, EJ ;
CASANOVA, J ;
VATAKENCHERRY, PA ;
WINTER, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :169-&
[9]  
DENO NC, 1961, TETRAHEDRON LETT, P414
[10]   USE OF A MODEL FOR RING-CURRENT EFFECT IN ANALYSIS OF NUCLEAR MAGNETIC RESONANCE SPECTRA OF DI- AND TRIPHENYLCYCLOPROPENIUM IONS [J].
FARNUM, DG ;
WILCOX, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5379-&
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