Source:http://linkedlifedata.com/resource/pubmed/id/12149022
Switch to
| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
31
|
| pubmed:dateCreated |
2002-7-31
|
| pubmed:abstractText |
An original approach to helicene frameworks exploiting atom economic isomerization of appropriate energy-rich aromatic cis,cis-dienetriynes has been developed. The new paradigm provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key cis,cis-dienetriynes and their nickel(0)-catalyzed [2+2+2] cycloisomerization. The potential of the methodology is underlined by the syntheses of the parent [5]helicene (2), 7,8-dibutyl[5]helicene (23), [6]helicene (24), and [7]helicene (25). The approach can be adapted to prepare functionalized helicenes as exemplified by the eight-step synthesis of 7,8-dibutyl-2,3-dimethoxy[6]helicene (34). Density functional theory (DFT) calculations showed that bis[2-((1Z)-1-buten-3-ynyl)phenyl]acetylene (1) and isomeric [5]helicene (2) differ enormously in the Gibbs energy content (DeltaG = -136.6 kcal x mol(-1)) to favor highly the devised intramolecular simultaneous construction of three aromatic rings.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
|
| pubmed:month |
Aug
|
| pubmed:issn |
0002-7863
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:day |
7
|
| pubmed:volume |
124
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
9175-80
|
| pubmed:dateRevised |
2003-11-3
|
| pubmed:year |
2002
|
| pubmed:articleTitle |
Synthesis of [5]-, [6]-, and [7]helicene via Ni(0)- or Co(I)-catalyzed isomerization of aromatic cis,cis-dienetriynes.
|
| pubmed:affiliation |
Institute of Organic Chemistry and Biochemistry and Center for Complex Molecular Systems and Biomolecules, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
|
| pubmed:publicationType |
Journal Article
|