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Electron impact induced fragmentation of dihydro-1,4-oxathiines. 1. 2,3-substituted 5,6-dihydro-1,4-oxathiines

✍ Scribed by Vesa Nevalainen; Pirjo Vainiotalo

Publisher: John Wiley and Sons
Year: 1986
Tongue: English
Weight: 709 KB
Volume: 21
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210210904

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✦ Synopsis

In the electron impact induced fragmentation of 2,3-disubstituted 5,6-dihydro-1,4-oxathiines, the cleavage of the heterocyclic ring proceeds through the retro Diels-Alder type of reaction. The further fragmentation of the resulting radical cation gives rise to substituted carbonyl or thiocarbonyl cations. This fragmentation favours the formation of an ion which, in the electron-deficient carbon-oxygen or carbon-sulphur triple bond, is stabilized by an electron-releasing group. The ring fragmentation was observed to be dependent on the nature of the 3-substituent of the ring when a series of 3-substituted 5,6-dihydro-2-methyl-l,I-oxathiines was investigated.

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