Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 49, Pages 20037-20040Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja310440e
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Funding
- National Science Foundation [CHE-1012914]
- Clare Booth Luce Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1012914] Funding Source: National Science Foundation
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Benzylidenecarbene was generated from a new photochemical source, 1-benzylidene-1a,9b-dihydro-1H-cyclopropa[l]phenanthrene, in deuterated benzene at ambient temperature. The carbene undergoes a facile rearrangement to phenylacetylene and could not be trapped by olefins. Generation of the carbene bearing a C-13 label at the beta-carbon produced phenylacetylene in which the label was found exclusively at the carbon adjacent to the phenyl ring. This overwhelming preference for H shift is consistent with B3LYP and CCSD(T) calculations. The label distribution observed in this work, however, contrasts previously reported high-temperature flash vacuum pyrolysis results where the interconversion of carbene and alkyne leads to the scrambling of labels over both alkynyl (sp) carbons.
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