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The oxygen rearrangement of aromatic and unsaturated esters under electron‐impact—I: General regularities of the rearrangement
Author(s) -
Kadentsev V. I.,
Zolotarev B. M.,
Chizov O. S.,
Shachidayatov Ch.,
Yanovskaya L. A.,
Kucherov V. F.
Publication year - 1968
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210010613
Subject(s) - chemistry , ketene , oxygen , molecule , rearrangement reaction , photochemistry , residue (chemistry) , alcohol , carroll rearrangement , reaction mechanism , medicinal chemistry , organic chemistry , sigmatropic reaction , catalysis
Some esters of γ, δ‐unsaturated or β‐arylsubstituted acids undergo a peculiar transformation under electron‐impact including an elimination of the alcohol residue as a radical R. with the following loss of the ketene molecule. One of the oxygen atoms of the carbonyl group enters an ion which is formed from an unsaturated part of the molecule. The possible mechanism of this reaction and the influence of structural modifications on the course of this process are discussed.