| On the existence of uncharged molecules with a pyramidally coordinated carbon: the cases of pentacyclo[4.3.0.0(2,9).0(3,8).0(7,9)]non-4-ene and heptacyclo- [7.6.0.0(1,5).0(5,15).0(6,14).0(10,14).0(10,15)]pentadecane. | |
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MedLine Citation:
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PMID: 16323874 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] B3LYP/6-31G(d) and MP2 calculations predict interactions between the divalent carbon and one double bond in tricyclo[3.2.2.0(2,4)]nona-6,8-dien-3-ylidene (3). Carbene 3 easily forms the more stable 4, a species with a pyramidal geometry. Moreover, the kinetic stability of 4 has been investigated, and some of its decay products are described. Interestingly, 3,3-dibromotricyclo[3.2.2.0(2,4)]nona-6,8-diene (1), the precursor of carbenoid 3, has already been reported and shown to undergo a formal dimerization to give 2. In addition, 15, a compound structurally related to 4, is expected to have a substantially greater stability toward further rearrangement. |
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Authors:
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Jean-Luc Mieusset; Udo H Brinker |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 70 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2005 Dec |
Date Detail:
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Created Date: 2005-12-05 Completed Date: 2006-06-14 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 10572-5 Citation Subset: - |
Affiliation:
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Institut f?r Organische Chemie, Universit?t Wien, W?hringer Strasse 38, A-1090 Wien, Austria. |
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