Studies in Mass Spectrometry. XIII.1 Stereospecific Electron Impact Induced Fragmentation Processes in Some Tricyclic Diesters

Joseph Deutsch, Asher Mandelbaum

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

endo-Dimethyl esters la, 2a, 3a, and 4a undergo elimination of methanol under electron impact through a seven-centered transition state. Stereoisomeric exo diesters lb, 2b, 3b, and 4b do not appreciably eliminate methanol. Loss of methoxyl radical from the molecular ion has been observed instead. trans-Diesters lc, 2c, 3c, and 4c eliminate methanol under electron impact through a five-centered transition state. An additional stereospecific hydrogen migration accompanying retro-Diels-Alder fragmentation has been observed in the endo isomers.

Original languageEnglish
Pages (from-to)4288-4291
Number of pages4
JournalJournal of the American Chemical Society
Volume92
Issue number14
DOIs
StatePublished - 1 Jul 1970
Externally publishedYes

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