Thermal rearrangements of heteroatom-bridged diallenes

被引：6

作者：

Bui, Binh H. ^{[1
]}

Schreiner, Peter R.

机构：

[1] Univ Georgia, Dept Chem, Athens, GA 30605 USA

[2] Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 18期

关键词：

computational chemistry; diallenes; heterocycles; radicals; rearrangement;

D O I：

10.1002/ejoc.200600270

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A systematic application of the BLYP/6-311+G*//BLYP/6-31G* computational scheme was utilized to identify the favored aromatic 2,6-reactions leading to the formally aromatic hetero-3,4-dimethylenecyclopentadienediyl derivatives from the thermal rearrangements of (hetero)atom-bridged diallenes (X = CH-, NH, O, S). Protonation of the heteroatom substituent raises the respective 2,6-cyclization energy barrier, and the alternative 1,6-cyclization reaction forming the hetero-cyclohexadienediyl can compete. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4187 / 4192

页数：6

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