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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>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub><jats:sup>−</jats:sup>COCH<jats:sub>3</jats:sub>→ [(<jats:italic>p</jats:italic>‐CH<jats:sub>3</jats:sub>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NCO)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>OC<jats:sub>6</jats:sub>H<jats:sub>4</jats:sub>NCO+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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