Unusual cross-ring SN2 reactions of [M-H]⁻ ions of methoxyacetanilides

Blanksby, S.; Dua, S.; Bowie, J.

Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/4847

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Type:	Journal article
Title:	Unusual cross-ring SN2 reactions of [M-H]⁻ ions of methoxyacetanilides
Other Titles:	Unusual cross-ring SN2 reactions of [M-H](-) ions of methoxyacetanilides
Author:	Blanksby, S. Dua, S. Bowie, J.
Citation:	Rapid Communications in Mass Spectrometry, 1995; 9(2):177-179
Publisher:	Heyden
Issue Date:	1995
ISSN:	0951-4198 1097-0231
Statement of Responsibility:	Stephen J. Blanksby, Suresh Dua and John H. Bowie
Abstract:	<jats:title>Abstract</jats:title><jats:p>Deprotonated <jats:italic>o, m</jats:italic>‐, and <jats:italic>p</jats:italic>‐methoxyacetanilide show pronounced peaks in their collision‐induced tandem mass spectra (MS/MS) produced by losses of the elements of C<jats:sub>2</jats:sub>H<jats:sub>6</jats:sub>. It is proposed that this reaction is a ‘cross‐ring’ internal S<jats:sub>N</jats:sub>2 reaction involving an incipient methyl anion. For example, <jats:italic>p</jats:italic>‐CH<jats:sub>3</jats:sub>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub><jats:sup>−</jats:sup>COCH<jats:sub>3</jats:sub>→ [(<jats:italic>p</jats:italic>‐CH<jats:sub>3</jats:sub>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NCO)CH<jats:inline-graphic xmlns:xlink="http://www.w3.org/1999/xlink" xlink:href="graphic/tex2gif-stack-1.gif" xlink:title="urn:x-wiley:09514198:media:RCM1290090214:tex2gif-stack-1" />]→<jats:sup>−</jats:sup>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NCO+C<jats:sub>2</jats:sub>H<jats:sub>6</jats:sub>.</jats:p>
Rights:	© 1995 John Wiley & Sons, Ltd.
DOI:	10.1002/rcm.1290090214
Published version:	http://dx.doi.org/10.1002/rcm.1290090214
Appears in Collections:	Aurora harvest 6 Chemistry publications

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