Source:http://linkedlifedata.com/resource/pubmed/id/11322541
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
6
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| pubmed:dateCreated |
2001-4-26
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| pubmed:abstractText |
A copper-mediated procedure for terminal alkynyl-propargyl coupling has been applied to "skipped" bis-terminal undecatetrayne and 1,4-bis(pseudo)halobut-2-ynes with the aim of preparing ring carbomers of representative strained and loose cycloalkanes, namely [N]pericyclynes. Two unprecedented, cyclic. "skipped" polyynes with CH2 vertices have been isolated as mixtures of diastereoisomers: an isomer 1b and a dimer 2a of [5]pericyclyne 1a. The isomer 1b is a cyclotetrayne with an exocyclic allene function resulting from a unique formal SN process. Its structure has been established by 1H/13C HMQC and HMBC two-dimensional NMR analysis. According to density functional theory calculations, it is about 6 kcalmol(-1) more stable than [5]pericyclyne (1a). Compound 1b can also be regarded as a C13-relaxed [4]pericyclyne, a long sought "skipped" C12 tetrayne. The dimer 2a is a C30 ring that results from a formal SN process. It is a stable ring carbomer of cyclodecane, that is, a [10]pericyclyne, with four CH2 vertices.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Mar
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| pubmed:issn |
0947-6539
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
16
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| pubmed:volume |
7
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
1165-70
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| pubmed:dateRevised |
2009-8-4
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| pubmed:year |
2001
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| pubmed:articleTitle |
On ring carbomers of cyclobutane, cyclopentane, and cyclodecane and cyclization reactions through bis(alkynyl-propargyl) coupling.
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| pubmed:affiliation |
Laboratoire de Chimie de Coordination, UPR 8241, Toulouse, France. chauvin@lcc-toulouse.fr
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| pubmed:publicationType |
Journal Article
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