Intramolecular dehydro Diels-Alder reactions of diarylacetylenes:: Switching between benzo[b]- and benzo[c]fluorenones as products by controlling the rearrangement of cyclic allene intermediates

被引：66

作者：

Rodríguez, D

Martínez-Esperón, MF

Navarro-Vázquez, A

Castedo, L

Domínguez, D

Saá, C

机构：

[1] Univ Santiago de Compostela, CSIC, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, CSIC, Fac Quim, Unidad Asociada, Santiago De Compostela 15782, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 11期

关键词：

D O I：

10.1021/jo0498213

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermal cyclization of 1-[2-(arylethynyl)phenyl]-3-trimethylsilylpropynones affords a mixture of benzo [b] fluorenones and benzo [c] fluorenones. The ratio of the two isomers can be efficiently varied between 100:0 and 0:100 by introducing substituents with appropriate electronic and steric properties on the aryl rings and using an appropriate solvent.

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页码：3842 / 3848

页数：7

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