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Aryne Cycloaddition with Stable Münchnones: Synthesis of 9,10‐Dihydro‐9,10‐epiminoanthracenes and Isoindoles

Aryne Cycloaddition with Stable Münchnones: Synthesis of 9,10‐Dihydro‐9,10‐epiminoanthracenes and... Arynes react with stable münchnones in a [3+2] cycloaddition/[4+2] cycloreversion sequence under mild conditions. The reaction initially affords isoindoles, but in the presence of excess arynes, these isoindole intermediates readily undergo a further aryne [4+2] cycloaddition to afford 9,10‐dihydro‐9,10‐epiminoanthracenes in good to excellent yields. Controlling the reaction conditions to stop at the isoindole stage was attempted but proved difficult and limited. This chemistry further expands aryne dipolar cycloaddition chemistry with mesoionic substrates. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Aryne Cycloaddition with Stable Münchnones: Synthesis of 9,10‐Dihydro‐9,10‐epiminoanthracenes and Isoindoles

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References (14)

Publisher
Wiley
Copyright
Copyright © 2014 Wiley Subscription Services, Inc., A Wiley Company
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201300221
Publisher site
See Article on Publisher Site

Abstract

Arynes react with stable münchnones in a [3+2] cycloaddition/[4+2] cycloreversion sequence under mild conditions. The reaction initially affords isoindoles, but in the presence of excess arynes, these isoindole intermediates readily undergo a further aryne [4+2] cycloaddition to afford 9,10‐dihydro‐9,10‐epiminoanthracenes in good to excellent yields. Controlling the reaction conditions to stop at the isoindole stage was attempted but proved difficult and limited. This chemistry further expands aryne dipolar cycloaddition chemistry with mesoionic substrates.

Journal

Asian Journal of Organic ChemistryWiley

Published: Jan 1, 2014

Keywords: ; ; ; ;

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