UNSPECIFIED (1993) UNIMOLECULAR REACTIONS OF ISOLATED ORGANIC IONS - LOSS OF CARBON-MONOXIDE FROM THE OXONIUM ION CH2=CHCH2+O=CH2 VIA DOUBLE HYDROGEN TRANSFER. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (3). pp. 501-507. ISSN 0300-9580

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Abstract

The reactions of the metastable oxonium ion CH2=CHCH2+O=CH2 have been investigated. This C4H7O+ species was generated by ionisation and alkyl radical loss from allyl ethyl or allyl propyl ether. CH2=CHCH2 +O=CH2 is apparently ideally suited to fragmentation via simple cleavage to form the favourable products CH2=CHCH2+ and CH2O. However, at low internal energies, expulsion of a neutral species having a mass of 28 amu takes place essentially to the exclusion of CH2O loss. H-2- and C-13-labelling experiments reveal that it is carbon monoxide which is eliminated, via double hydrogen transfer between the developing products accessible to C-O bond fission. The role of ion-neutral complexes in these hydrogen transfer steps is discussed.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Journal or Publication Title:	JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Publisher:	ROYAL SOC CHEMISTRY
ISSN:	0300-9580
Date:	March 1993
Number:	3
Number of Pages:	7
Page Range:	pp. 501-507
Publication Status:	Published
URI:	http://wrap.warwick.ac.uk/id/eprint/21500

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