Syntheses, thermal reactivities, and computational studies of aryl-fused quinoxalenediynes: effect of extended benzannelation on Bergman cyclization energetics

…, S Chavez, R Fernandez, BF Gherman

Index: Spence, John D.; Rios, Andro C.; Frost, Megan A.; McCutcheon, Claire M.; Cox, Christopher D.; Chavez, Sonia; Fernandez, Ramiro; Gherman, Benjamin F. Journal of Organic Chemistry, 2012 , vol. 77, # 22 p. 10329 - 10339

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Citation Number: 13

Abstract

A series of [b]-fused 6, 7-diethynylquinoxaline derivatives have been synthesized through an imine condensation strategy to examine the effect of extended benzannelation on the thermal reactivity of enediynes. Absorption and emission spectra of the highly conjugated quinoxalenediynes were red-shifted approximately 100–200 nm relative to those of 1, 2- diethynylbenzene. Strong exotherms indicative of enediyne cyclization were observed by ...