Document Detail

On the existence of uncharged molecules with a pyramidally coordinated carbon: the cases of pentacyclo[,9).0(3,8).0(7,9)]non-4-ene and heptacyclo- [,5).0(5,15).0(6,14).0(10,14).0(10,15)]pentadecane.
MedLine Citation:
PMID:  16323874     Owner:  NLM     Status:  PubMed-not-MEDLINE    
[reaction: see text] B3LYP/6-31G(d) and MP2 calculations predict interactions between the divalent carbon and one double bond in tricyclo[,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[,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.
Jean-Luc Mieusset; Udo H Brinker
Related Documents :
18376864 - A general synthetic entry to the pentacyclic strychnos alkaloid family, using a [4 + 2]...
25479334 - Protonated polycyclic aromatic nitrogen heterocyclics: proton affinities, polarizabilit...
22635044 - Giant magnetocaloric effect driven by structural transitions.
16995674 - Efficient trans-selectivity in the cyclocondensation of (s)-2-[2-(p-tolylsulfinyl)pheny...
21200844 - 4-[4-(methyl-sulfan-yl)phen-yl]-6-phenyl-2,2'-bipyridine.
22213474 - Aerobic palladium(ii)-catalyzed 5-endo-trig cyclization: an entry into the diastereosel...
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:  -    
Institut f?r Organische Chemie, Universit?t Wien, W?hringer Strasse 38, A-1090 Wien, Austria.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Facile synthesis, structure, and properties of benzo[1,2-b:4,5-b']dichalcogenophenes.
Next Document:  De novo asymmetric syntheses of D- and L-talose via an iterative dihydroxylation of dienoates.