The gas-phase Wittig–oxy Cope rearrangement of deprotonated diallyl ether
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1499-1502
- https://doi.org/10.1039/p29870001499
Abstract
Collisional activation of deprotonated diallyl ether is found to give major products formd by competitive losses of H2, C3H4O and C4H6. Products are rationalised in terms of the Wittig-oxy Cope rearrangement sequence CH2 CH–H–O–allyl →(CH2 CH)(CH2 CH–CH2)CHO–→ CH2 CH(CH2)2 CHCHO → products. The spectrum of CH2 CH–CDOCD2CHCH2 shows the operation of both 1,2- and 1,4-Witting rearrangements, while that of CH2 CH–CDO–allyl shows proton transfer (to form CH2 CH–CHD–O–HCHCH2) to be a minor process.Keywords
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