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Four‐centred rearrangements in the mass spectra of aliphatic ethers
Author(s) -
Tsang C. W.,
Harrison A. G.
Publication year - 1970
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.1210030512
Subject(s) - fragmentation (computing) , mass spectrum , chemistry , ether , alkyl , metastability , ion , stereochemistry , medicinal chemistry , organic chemistry , computer science , operating system
The [CH 3 OCHCH 3 ] + ions observed in the mass spectra of ethers of formula CH 3 OCH (CH 3 )R(R = H or alkyl) undergo two rearrangement fragmentation reactions to form [C 2 H 5 ] + and [CH 2 OH] + . The scope of the rearrangements has been investigated and it is shown that enlargement of the alkyl group on either side of the ether linkage leads to alternative fragmentation routes. From a study of metastable intensities it is concluded that the fragmentations probably occur directly from the [CH 3 OCHCH 3 ] + structure through four centred rearrangements rather than through the intermediacy of the [C 2 H 5 OCH 2 ] + ion.