C–C Bond Activation and Demethylenation of Epoxides by Amine Radical Dications

In this note, we explore a unique reactivity pattern that involves a rare radical-based C–C bond scission of epoxides followed by demethylenation. The reaction is accomplished by Selecfluor and its radical dication working in tandem; a mechanism supported by experiment and DFT calculations is propos...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 88; no. 11; pp. 7597 - 7600
Main Authors:	Holt, Eric, Garrison, Nathaniel G., Rowshanpour, Rozhin, Kim, Justin Jeeyoung, Henriquez, Nicolas, Lam, Winson, Kiame, Neil, Williams, Jack, Zhao, Sherrie, Dudding, Travis, Lectka, Thomas
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 02-06-2023
Online Access:	Get full text
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Summary:	In this note, we explore a unique reactivity pattern that involves a rare radical-based C–C bond scission of epoxides followed by demethylenation. The reaction is accomplished by Selecfluor and its radical dication working in tandem; a mechanism supported by experiment and DFT calculations is proposed that involves the generation and identification of a key reactive intermediate. The reaction seems to be fairly general for 1,1-disubstituted epoxides.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.3c00605