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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.
MedLine Citation:
PMID:  16323874     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
[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.
Authors:
Jean-Luc Mieusset; Udo H Brinker
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Dec 
Date Detail:
Created Date:  2005-12-05     Completed Date:  2006-06-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  10572-5     Citation Subset:  -    
Affiliation:
Institut f?r Organische Chemie, Universit?t Wien, W?hringer Strasse 38, A-1090 Wien, Austria.
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