Isomerization of thioamidomethyl pyridine ylides and isoquinoline ylides under electron impact

Eur. J. Mass Spectrom. 3, 217–223 (1997)
DOI: 10.1255/ejms.14

Isomerization of thioamidomethyl pyridine ylides and isoquinoline ylides under electron impact

A.T. Lebedev,^* T.Yu. Samguina, E.V. Predein and V.A. Bakoulev
Department of Chemistry, Moscow State University, Moscow, Russia 119899.
N. Tretyakova and J.R. Hass
Department of Environmental Science & Engineering, University of North Carolina at Chapel Hill, NC 27599, USA.

ABSTRACT:

The electron impact and collision-induced dissociation spectra of 2-(2-carbethoxy-1-imino-1-methylthio)-ethylene isoquinoline ylide (1), 2-(2-cyano-1-phenylamino-1-methylthio)-ethylene pyridine ylide (2), 2-(2-carboethoxy-1-amino-1-thio)-ethylene pyridine ylide (3),2-(2-carboethoxy-1-amino-1-thio)-ethylene isoquinoline ylide (4) and 2-(1-N-phenylamide-1-cyano)- ethylene pyridine ylide (5) were studied.The molecular ions of compounds 1–4 were shown to undergo cyclization to the corresponding heterocyclic compounds, analogous to the reaction of compound 1 in solution. Proposed fragmentation schemes are presented based on tandem mass spectrometry and high resolution mass spectrometry data.

Keywords: Intramolecular cyclization, ylides, electron impact,collision-induced dissociation, pyridines, isoquinolines, isomerization.

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