Mass spectral hydrogen rearrangements of 1,1′‐bicycloalkyldiols under electron impact

Joseph Deutsch*, Miriam Chriki

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

1,1′‐Bicycloalkyl‐2,2′‐diols (mixtures of stereoisomers) and 1,1′‐diols on electron impact give rise to strong peaks equivalent to [M‐1]+ions, corresponding to cycloalkenone fragments and obviously involving hydrogen atom migrations. Deuterium labelling and substitution techniques reveal the operation of different rearrangement mechanisms for the two series of isomeric compounds. Thus, in the 1,1′‐bicycloalkyl‐2,2′‐diols a ring hydrogen atom is involved in the rearrangement, whereas in the 1,1′‐bicycloalkyl‐1,1′‐diols (pinacols) the hydroxylic hydrogen atoms migrate.

Original languageEnglish
Pages (from-to)482-484
Number of pages3
JournalJournal of Mass Spectrometry
Volume14
Issue number9
DOIs
StatePublished - Sep 1979

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