Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases p. 2511 - 2518 (1988)
Update date:2022-08-05
Topics:
Clarke, John K. A.
Hegarty, Bernard F.
Rooney, John J.
Reactions of 1,1,3,3-tetramethylcyclobutane (TMCB)-hydrogen mixtures on evaporated metal films have shown that both ring scission to 2,2,4-trimethylpentane (TMP) and ring enlargement to 1,1,3-trimethylcyclopentane (TMCP) are dominant on sintered platinum films, while ring scission to TMP predominates on sintered palladium and on unsintered molybdenum films.Unsintered tantalum and molybdenum films gave a large production of iC4 hydrocarbon, particularly above ca. 500 K: ring enlargement was a minor reaction found particularly with tantalum.The homogeneous reaction of TMCB giving a large iC4 production sets in at 600 K.The possibility, suggested by the product distribution, that the reaction of TMCB on Mo and Ta is a metal-assisted free-radical reaction is examined.While it may not be completely excluded that the catalysed ring enlargement on Pt and Pd is a free-radical reaction it is argued that only the previously proposed Rooney-Samman bond-shift mechanism accommodates without added qualifications published facts on bond shifts, including those at quaternary carbon atoms, and also ring enlargements.
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