Linked Life Data

16468802

Source:http://linkedlifedata.com/resource/pubmed/id/16468802

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
4
pubmed:dateCreated
2006-2-10
pubmed:abstractText
Upon treatment with BF3.Et2O at low temperature, enantiopure benzyl-type ethers of arylglycidols with electron withdrawing substituents at the skeletal aryl group and electron donating substituents at the benzyl group undergo stereospecific rearrangements of Friedel-Crafts type, leading to enantiopure 4-diarylmethyl-1,3-dioxolanes (2) or to enantiopure trans-4,5 disubstituted tetrahydrobenzo[c]oxepin-4-ols (5). The course of the reactions is controlled by the substitution pattern at the benzyl ether: While benzylic systems activated toward ipso substitution afford diarylmethanes 2 through a Friedel-Crafts reaction followed by fragmentation, benzylic systems activated toward ortho attack lead to enantiopure oxepinols 5 through a 7-endo-tet ring closure of Friedel-Crafts type.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0022-3263
pubmed:author
pubmed:issnType
Print
pubmed:day
17
pubmed:volume
71
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1537-44
pubmed:meshHeading
pubmed:year
2006
pubmed:articleTitle
Boron trifluoride-induced, new stereospecific rearrangements of chiral epoxy ethers. Ready access to enantiopure 4-(diarylmethyl)-1,3-dioxolanes and 4,5-disubstituted tetrahydrobenzo[c]oxepin-4-ols.
pubmed:affiliation
Departament de Química Orgànica and Parc Científic de Barcelona, Universitat de Barcelona, 08028 Barcelona, Spain.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't