The thermal retro[2+2+2]cycloaddition of cyclohexane activated by triscyclobutenannelation:: Concerted all-disrotatory versus stepwise conrotatory pathways to fused [12]Annulenes

被引：17

作者：

Eichberg, Michael J.

Houk, K. N.

Lehmann, Juerg

Leonard, Philip W.

Maerker, Anne

Norton, Joseph E.

Sawicka, Dorota

Vollhardt, K. Peter C. ^{[1
]}

Whitener, Glenn D.

Wolff, Stefan

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Lawrence Berkeley Natl Lab, Div Chem Sci, Berkeley, CA 94720 USA

[3] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 36期

关键词：

ab initio calculations; cage compounds; electrocyclic reactions; isomerization; strained molecules;

D O I：

10.1002/anie.200702474

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) All dis or all con? While benzo analogues 2-4 undergo cycloreversion of the central cyclohexane ring by all-disrotatory opening, the triscyclobutenocyclohexane 1 does so by stepwise conrotatory cyclobutane rupture. This remarkable conclusion is based on DFT calculations carried out in conjunction with experiments. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6894 / 6898

页数：5

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[1]

[Anonymous], Gaussian 03, Revision C.02 Gaussian, inc., wallingford, ct

[2]

BANCIU MD, 1991, REV ROUM CHIM, V36, P1101

[3] CHEMISTRY OF 1,2-5,6-DIBENZOCYCLOOCTATETRAENE DIANION [J].