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

…, JM Wright, G Hynd, JK Wyatt, PM Warner…

Index: Jones, Graham B.; Wright, Justin M.; Hynd, George; Wyatt, Justin K.; Warner, Philip M.; Huber, Robert S.; Li, Aiwen; Kilgore, Michael W.; Sticca, Robert P.; Pollenz, Richard S. Journal of Organic Chemistry, 2002 , vol. 67, # 16 p. 5727 - 5732

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Citation Number: 31

Abstract

Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).