How to Lose a Bond in Two Ways - The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions

被引：79
作者：
Peterson, Paul W. [1 ]
Mohamed, Rana K. [1 ]
Alabugin, Igor V. [1 ]
机构：
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 13期
基金：
美国国家科学基金会;
关键词：
Cycloaromatization; Zwitterions; Radicals; Reaction mechanisms; MEDIATED ELECTROPHILIC CYCLIZATION; THERMAL BIRADICAL CYCLIZATIONS; INTRAMOLECULAR CHARGE-TRANSFER; SELF-ASSEMBLED MONOLAYERS; ENEDIYNE MODEL COMPOUNDS; BERGMAN CYCLIZATION; ENYNE-ALLENES; MYERS-SAITO; DNA CLEAVAGE; SUBSTITUTED ISOQUINOLINES;
D O I：
10.1002/ejoc.201201656
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cycloaromatization reactions decouple two electrons by breaking two bonds to form only one sigma bond and illustrate one of the most common mechanistic dichotomies in chemistry, namely the two ways of breaking a chemical bond: Zwitterionic or diradical. With a suitable choice of reaction conditions, substitution patterns, and catalysts, cycloaromatization processes can be redirected from the usual formation of a diradical towards a variety of zwitterionic pathways. This review illustrates the practical approaches for directing zwitterionic cycloaromatization reactions and lays the mechanistic foundations for the further development of this emerging field.
引用
收藏
页码：2505 / 2527
页数：23
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