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

GW Plourde, PM Warner, DA Parrish…

Index: Plourde II, Gary W.; Warner, Philip M.; Parrish, Dennis A.; Jones, Graham B. Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5369 - 5374

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Citation Number: 31

Abstract

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 ...