Intramolecular [4+2] cycloaddition reactions of diarylacetylenes:: Synthesis of benzo[b]fluorene derivatives via cyclic allenes

被引：92

作者：

Rodríguez, D

Navarro, A

Castedo, L

Domínguez, D

Saá, C

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15706, Spain

[2] Univ Santiago de Compostela, Fac Quim, CSIC, Unidad Asociada, Santiago De Compostela 15706, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 11期

关键词：

D O I：

10.1021/ol991391t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 2-Propynyldiarylacetylenes undergo thermal intramolecular [4 + 2] cycloaddition to give benzo[b]fluorene derivatives in good yields. The hybridization of the tether connecting the reacting alkynes has a pronounced effect on the course of the reaction. Theoretical calculations and isotopic labeling studies support a mechanism which involves the generation of a cyclic allene intermediate that evolves to the final benzo[b]fluorene.

引用

页码：1497 / 1500

页数：4

共 28 条

[1] PHENYLPROPIOLIC ACIDS .6. THE CYCLISATION OF DISSIMILARLY SUBSTITUTED PHENYLPROPIOLIC ANHYDRIDES TO THE CORRESPONDING 1-PHENYLNAPHTHALENES [J].