MECHANISM OF KETENE FORMATION FROM CYCLOHEXENONES UPON ELECTRON IMPACT . CORRELATIONS WITH PHOTOCHEMISTRY

被引:21
作者
FENSELAU, C
DAUBEN, WG
SHAFFER, GW
VIETMEYE.ND
机构
[1] Department of Chemistry, Space Science Laboratory, University of California, Berkeley
关键词
D O I
10.1021/ja01029a024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The high-resolution mass spectra and the metastable ions of a number of alkyl-substituted 2-cyclohexenones and related bicyclic and steroidal unsaturated ketones, together with deuterium-labeled analogs, have been measured and the course and the scope of electron impact induced rearrangements and fragmentations occurring in these compounds discussed. A similar study of alkyl-substituted bicyclo[3.1.0]hexan-2-ones, derived from the cyclohexenones by photochemical transformation, is reported. A variety of data support the postulate that on electron impact, a portion of the molecular ions of 2-cyclohexenones rearrange to molecular ions resembling those formed from related bicyclo[3.1.0]hexan-2-ones, and it is from these rearranged ions that ketene is eliminated. © 1969, American Chemical Society. All rights reserved.
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页码:112 / &
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