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The loss of a methyl radical and the retro diels—Alder reaction in the electron impact mass spectrometry of 2-cyclohexen-1-ol and related compounds

✍ Scribed by Deniel Braem; Fazil O. Gülaçar; Ulrich Burger; Armand Buchs

Publisher: John Wiley and Sons
Year: 1979
Tongue: English
Weight: 754 KB
Volume: 14
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210141108

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✦ Synopsis

Abstract

The electron impact mass spectra of 2‐cyclohexen‐1‐ol and of several of its ^2^H and ^13^C labelled analogues show that the molecular ions lose a methyl radical by a completely different means from the mechanism described previously. Moreover, the retro Diels–Alder reaction also proceeds in a non‐classical way; in addition to the elimination of an olefinic molecule from unrearranged molecular ions, a second more important route implies a formal 1,3 allylic rearrangement prior to the retro Diels–Alder reaction. The mass spectra of a series of alkyl substituted homologues show that the competition between the two processes is closely related to the size of the olefinic moiety that is expelled.

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