Can bridged 1,6-X-[10]annulenes (X = SiH2, SiMe2, PH, and S) exist?

被引：17

作者：

Jiao, HJ

Hommes, NJRV

Schleyer, PV ^{[1
]}

机构：

[1] Shanxi Normal Univ, Dept Chem, Linfen 041004, Peoples R China

[2] Univ Rostock, Inst Organ Katalyseforsch, D-18055 Rostock, Germany

[3] Univ Erlangen Nurnberg, Comp Chem Ctr, D-91052 Erlangen, Germany

[4] Univ Georgia, Dept Chem, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 14期

关键词：

D O I：

10.1021/ol026144v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the 1,6-X-[10]annulenes (X = CH2, O, NH) with delocalized forms (c), their X = PH and S counterparts favor the bisnorcaradiene structures (b). Forms b and c are close in energy with X = SiH2 and Web The computed nucleus independent chemical shifts (NICS), show both annuienes (c) and cyclic polyenes (a) to be aromatic. Strain-introduced structural localization, e.g., due to four bulky SiMe3 substituents, reduces but does not eliminate aromaticity.

引用

页码：2393 / 2396

页数：4

共 39 条

[1] ON THE EQUILIBRIUM [10]ANNULENE REVERSIBLE BISNORCARADIENE - X-RAY STUDY OF THE BETA-FORM OF 11-METHYLTRICYCLO[4.4.1.01,6]UNDECA-2,4,7,9-TETRAENE-11-CARBONITRILE AT 2 TEMPERATURES [J].