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Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

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Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intertment41358Apparent Alkyl Transfer and Phenazine Formation via an Aryne IntermediateDaniel BeckerLoyola University Chicago, dbecke3@luc.eduAndria M. P

anagopoulosLoyola University ChicagoDoug SteinmanLoyola University ChicagoAlexandra GoncharenkoLoyola University ChicagoKyle Gearyfollow tỸi?sZẩnầ ucố Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

niorẵĩworks at: https://ecommons.luc.edu/chemistry_facpubsÒ* Part of the Chemistry CommonsÂtft Rồ¥rirtr'ona/ authorsThis is a pre-publication author m

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

anuscript of the final, published article.Recommended CitationBecker, Daniel; Panagopoulos, Andria M.; Steinman, Doug, Goncharenko, Alexandra; Geary,

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intenal of Organic Chemistry, 78.8:, 2013. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1021/jo30

2795wThis Article is brought to you for free and open access by the Faculty Publications and other Works by Department at Loyola eCommons. It has been Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

accepted for inclusion in Chemistry: Faculty Publications and other Works by an authorized administrator of Loyola eCommons. For more information, pl

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

ease contact ecommons@luc edu.This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License. © 2013 America

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inteisman, Elizabeth Spaargaren, and Matthias ZellerThis article is available at Loyola eCommons: https://ecommon5.luc edu/chemistry.facpubs/41Apparent Al

kyl Transfer and Phenazine Formation via an Aryne IntermediateAndria M. Panagopoulos.50 Doug Steinman.5 Alexandra Goncharenko.5 Kyle Geary?Carlenc Sch Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

leisman? Elizabeth spaargarcn? Matthias Zeller.’ and Daniel p. Becker5*'Department of Chemistry, Jjoyola University Chicago, 1032 IV. Sheridan Road. C

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

hicago, IL 60660. United States. Department of Chemistry, I University Plaza. Youngstown State University, Youngstown, Ohio 44555-3663, United Stalesi

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intel derivatives 3a and 3(1 or fluorotriaryl derivatives 3b and 3c with potassium di isopropyl am ide afforded alkyl-shifted phenazine derivatives 5a/5b.

rather than the expected 9-membered triaza ơrrAơcyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and a Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

lkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via. the interm

Apparent Alkyl Transfer and Phenazine Formation via an Aryne Inte

ediacy of the aryne intermediate.. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitteri

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

LOYOLAffl eCOMMONSLoyola University ChicagoLoyola eCommonsChemistry: Faculty Publications and other WorksFaculty Publications and other Works by Depar

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