Abstract
The reactions of the metastable oxonium ion CH2CHCH2+OCH2 have been investigated. This C4H7O+ species was generated by ionisation and alkyl radical loss from allyl ethyl or allyl propyl ether. CH2CHCH2+OCH2 is apparently ideally suited to fragmentation via simple cleavage to form the favourable products CH2CHCH2+ 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. 2H-and 13C-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.
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