Linked Life Data

12708862

Source:http://linkedlifedata.com/resource/pubmed/id/12708862

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
17
pubmed:dateCreated
2003-4-23
pubmed:abstractText
A novel transformation of silyl amides to N-cis-propenyl amides was recently reported, the reaction of which is a formal 10-electron double sigmatropic, or dyotropic, rearrangement. Density functional calculations (B3LYP/6-311++G(3d,3p)//B3LYP/6-31G(d)) have been carried out to investigate the mechanism of this reaction. A two-step process involving sequential 1,4-silyl and 1,4-hydrogen shifts is predicted. The 1,3-dipolar azomethine ylide intermediate profits from charge stabilization by allylic resonance and phenyl conjugation. The consecutive thermal migration of two sigma-bonds (stepwise dyotropic rearrangement) is an example of a host of reactions with synthetic potential.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Apr
pubmed:issn
0002-7863
pubmed:author
pubmed:issnType
Print
pubmed:day
30
pubmed:volume
125
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
5111-4
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
Mechanism of cis-enamide formation from N-(alpha-silyl)allyl amides: synthetic potential of stepwise dyotropic rearrangements.
pubmed:affiliation
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.