Halo-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization

被引：31

作者：

Plourde, GW ^{[1
]}

Warner, PM ^{[1
]}

Parrish, DA ^{[1
]}

Jones, GB ^{[1
]}

机构：

[1] Northeastern Univ, Dept Chem, Boston, MA 02115 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 15期

关键词：

D O I：

10.1021/jo025763e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of halogen-substituted cyclic enediynes were prepared with use of carbenoid coupling strategy. DFT analysis, initially used to identify synthesis candidates, was also employed to rationalize the propensity for cycloaromatization. of the compounds. In all cases studied the halogen atom had a strongly retardative effect on the thermal Bergman cycloaromatization. reaction. The isolation of the first C-9 monochloroenediyne is noteworthy, and may find application in prodrug design.

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页码：5369 / 5374

页数：6

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