ORGN 115 |
| Rearrangements of C3H4 isomers, which are relevant to combustion and interstellar chemistry, have been studied experimentally and computationally. We focused attention on vinylcarbene in an attempt to characterize this species, spectroscopically, and to probe the mechanism of its rearrangement to propyne. Irradiation (λ > 534 nm) of diazopropene under matrix isolation conditions affords a surprisingly complex product mixture, with only a small amount of triplet vinylcarbene detected by IR and ESR spectroscopy. Irradiation of diazopropene under different conditions (λ = 484 nm) affords an intermediate tentatively identified as propenylidene-3-d1 by comparison of experimental and computed IR spectra. The subsequent rearrangement (λ > 363 nm) of this species to propyne-3-d1 is also consistent with the propenylidene-3-d1 assignment.
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Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
