Comparison of the mass spectra of 6‐thiotheophyllines and 6‐sulfinytheophyllines

Felix Bergmann*, Miriam Rahat, Arie Frank, Joseph Deutsch

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Under electron impact, 6‐thiotheophyllines eliminate various fragments from the pyrimidine moiety. In a retro Diels‐Alder reaction, they lose the fragment XCNCH3 from positions 1 and 2 of the pyrimidine ring. In 6‐sulfinyltheophyllines, the sulfinyl group is the main target for fragmentation; it can lose either oxygen or sulfur, and the abundance of [M—16]+ and [M—32]+ is much higher than the abundance of the molecular ion. Elimination of the sulfur atom of the 6‐sulfinyl substituent, with retention of its oxygen, may be explained by intermediate formation of a ring. All further fragmentations of the 6‐sulfinyl derivatives proceed by a primary loss of oxygen or sulfur, followed by elimination of fragments from the pyrimidine moiety, similar to the primary processes, observed in the mass spectra of the 6‐thiotheophyllines.

Original languageEnglish
Pages (from-to)565-568
Number of pages4
JournalJournal of Mass Spectrometry
Volume17
Issue number11
DOIs
StatePublished - Nov 1982

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