Journal of Organic Chemistry p. 4494 - 4497 (1984)
Update date:2022-07-30
Topics:
Parker, Garth
Wiseman, Douglas
Wintner, Claude
MacKay, Colin
The gas-phase reaction of C2O(3Σ) with 2,3-dimethyl-2-butene produces 1,1,2,2,6,6,7,7-octamethyldispiro<2.1.2.1>octane-4,8-dione and 2,2,3,3-tetramethylcyclopropanecarboxylic acid as major products rather than the allenic product characteristic of the reaction with simpler substrates.The positive identification of these molecules provides strong evidence for prior formation of the previously postulated cyclopropylideneketene.Further, the rate-determining step for reaction of C2O(3Σ) with the substrate cannot be elimination of CO as has been postulated on the basis of calculations.
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