ELECTROPHILIC AROMATIC PROTONATION OF STABLE PI-CARBOCATIONS

被引:13
作者
PAGNI, RM
SMITH, RJ
机构
[1] Department of Chemistry, University of Tennessee Knoxville, Tennessee
关键词
D O I
10.1021/ja00496a052
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We noted with interest the recent report of a new type of electrophilic aromatic substitution: the reaction of H+ and D+ with an aromatic cyclopropenyl cation. This highly unusual reaction involves bringing together two positively charged species. We report here that the protonation of aromatic carbocations may be common and much more facile than anyone has imagined. © 1979, American Chemical Society. All rights reserved.
引用
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页码:506 / 508
页数:3
相关论文
共 9 条
[1]  
BETHELL D, 1967, CARBONIUM IONS INTRO, pCH4
[2]   BASIC STRENGTHS OF SOME AROMATIC ALDEHYDES AND KETONES [J].
CULBERTSON, G ;
PETTIT, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (06) :741-&
[3]  
ELANANI AA, 1970, CHEM COMMUN, P1024
[4]   TRIFLUOROMETHANESULFONIC ACID AND DERIVATIVES [J].
HOWELLS, RD ;
MCCOWN, JD .
CHEMICAL REVIEWS, 1977, 77 (01) :69-92
[5]   FACTORS INFLUENCING BASICITIES OF TRIARYLCARBINOLS SYNTHESIS OF SESQUIXANTHYDROL [J].
MARTIN, JC ;
SMITH, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (11) :2252-&
[6]   UNTERSUCHUNGEN IN DER BENZTROPYLIUM-REIHE .8. DAS SAURE-BASEN-GLEICHGEWICHT ZWISCHEN DEN BENZOLOGEN DES TROPYLIUM-KATIONS UND IHREN KONJUGATEN PSEUDOBASEN [J].
MEUCHE, D ;
STRAUSS, H ;
HEILBRONNER, E .
HELVETICA CHIMICA ACTA, 1958, 41 (01) :57-70
[7]  
PAGNI RM, UNPUBLISHED
[8]   FUNCTIONAL CYCLO C-3-DERIVATIVES .4. SE REACTIONS ON C+3-RING - PI-ATTACK [J].
WEISS, R ;
PRIESNER, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (06) :445-446
[9]   FUNCTIONAL CYCLO C-3-DERIVATIVES .5. SE REACTIONS ON C+3-RING - SIGMA-ATTACK [J].
WEISS, R ;
PRIESNER, C ;
WOLF, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (06) :446-447