Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases p. 1849 - 1856 (1980)
Update date:2022-07-29
Topics:
Carless, Howard A. J.
Maitra, A. Kumar
Pottinger, Ruth
Frey, Henry M.
The thermal decomposition of the title compound yields penta-1,3-diene and ethanal as major products when pyrolysed in the gas phase between 326 and 384 deg C.This fragmentation reaction is kinetically first order and probably occurs by a biradical mechanism.Arrhenius parameters have been determined for this decomposition: log k/S-1=13.42+/-0.60-(200.3+/-7.5kJ mol-1)/RTln10.As well as the major decomposition pathway there are several minor ones.A ring expansion reaction to yield 2,6 dimethyl-3,6-dihydro-2H-pyran and a trans-cis isomerization to trans-2,4-dimethyl-3-vinyloxetan both occur to the extent of from 2 to 3 percent of the fragmentation reaction.Both these compounds are themselves thermally unstable at the reaction temperatures.The results are compared with those reported for other oxetans and also for appropiately substituted cyclobutanes.
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