Unusual cross‐ring S N 2 reactions of [MH] −  ions of methoxyacetanilides | Zendy

Blanksby Stephen J. | Zendy; Dua Suresh | Zendy; Bowie John H. | Zendy

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Unusual cross‐ring S N 2 reactions of [MH] − ions of methoxyacetanilides

Author(s) -

Blanksby Stephen J.,

Dua Suresh,

Bowie John H.

Publication year - 1995

Publication title -

rapid communications in mass spectrometry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.528

H-Index - 136

eISSN - 1097-0231

pISSN - 0951-4198

DOI - 10.1002/rcm.1290090214

Subject(s) - chemistry , ion , ring (chemistry) , mass spectrum , deprotonation , tandem , analytical chemistry (journal) , medicinal chemistry , organic chemistry , materials science , composite material

Deprotonated o, m ‐, and p ‐methoxyacetanilide show pronounced peaks in their collision‐induced tandem mass spectra (MS/MS) produced by losses of the elements of C 2 H 6 . It is proposed that this reaction is a ‘cross‐ring’ internal S N 2 reaction involving an incipient methyl anion. For example, p ‐CH 3 OC 6 H 4 − COCH 3 → [( p ‐CH 3 OC 6 H 4 NCO)CH 3 − ]→ − OC 6 H 4 NCO+C 2 H 6 .

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