Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases p. 2185 - 2194 (1983)
Update date:2022-08-05
Topics:
Flowers, Michael C.
Honeyman, Malcolm R.
The photolyses of ketene (λ = 313 and 334 nm) and diazomethane (λ = 366 nm) in the presence of 2,3-dimethyl-2,3-epoxybutane (DMEB), oxygen and 2,2-dimethylpropane (as internal standard) have been investigated.Four main reaction products from DMEB were observed and identified: 2,3-dimethyl-2,3-epoxypentane (DMEP), 2,3-dimethylbut-2-ene, propanone and 2,3-dimethyl-2,3-epoxybutanal.CH2(1A1), formed from ketene or diazomethane, was found to insert into the C-H bonds of DMEB to give DMEP at 0.4 times the rate it inserted in to the C-H bonds of 2,2-dimethylpropane; however, no CH2(1A1) C-O insertion products were observed. 2,3-dimethylbut-2-ene and propanone were formed by pathways that did not involve methylene radicals and significant loss of 2,3-dimethylbut-2-ene, by secondary reactions, was observed in oxygen scavenged, ketene systems. 2,3-dimethyl-2,3-epoxybutanal was formed in both ketene and diazomethane systems but the amount produced varied with photolysis wavelength and methylene precursor.Mechanisms for the formation of all reaction products are discussed.
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