Does the Reaction of Cyclopropyl Acid Chlorides and Imines To Form 1,3-Oxazin-4-enone Heterocycles Proceed via a Ketene or an N-Acyl-iminium Mechanism?

Alexander J. Craig; Andrew P. Cording; Anna L. Garden; Bill C. Hawkins

doi:10.1021/acs.joc.0c00229

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Does the Reaction of Cyclopropyl Acid Chlorides and Imines To Form 1,3-Oxazin-4-enone Heterocycles Proceed via a Ketene or an N-Acyl-iminium Mechanism?

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Does the Reaction of Cyclopropyl Acid Chlorides and Imines To Form 1,3-Oxazin-4-enone Heterocycles Proceed via a Ketene or an N-Acyl-iminium Mechanism?

Alexander J. Craig, Andrew P. Cording, Anna L. Garden and Bill C. Hawkins

Journal of organic chemistry, Vol.85(8), pp.5486-5492

17/04/2020

DOI: https://doi.org/10.1021/acs.joc.0c00229

Abstract

Chemistry

Chemistry, Organic

Physical Sciences

Science & Technology

The mechanism of the reaction between cyclopropyl acid chlorides and imines to form 1,3-oxazin-4-enones was probed through physical and computational experiments. The data gathered strongly support the reaction proceeding through an N-acyl iminium intermediate mechanism rather than a ketene intermediate mechanism.

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Record Identifier: 9926495530501891
Title: Does the Reaction of Cyclopropyl Acid Chlorides and Imines To Form 1,3-Oxazin-4-enone Heterocycles Proceed via a Ketene or an N-Acyl-iminium Mechanism?
Creators: Alexander J. Craig
Andrew P. Cording
Anna L. Garden
Bill C. Hawkins
Publication Details: Journal of organic chemistry, Vol.85(8), pp.5486-5492
Academic Unit: Chemistry
Publisher: Amer Chemical Soc
Grant note: University of Otago
Date published ; e-published: 17/04/2020
Language: English
Resource Type: Journal article

Does the Reaction of Cyclopropyl Acid Chlorides and Imines To Form 1,3-Oxazin-4-enone Heterocycles Proceed via a Ketene or an N-Acyl-iminium Mechanism?

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