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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
6
pubmed:dateCreated
2009-1-5
pubmed:abstractText
The phase-vanishing (PV) method is based on spontaneous reaction controlled by diffusion of reagents into fluorous media, such as perfluorohexanes (FC-72) and polyperfluoroethers. Thus, the original PV reaction utilizes a triphasic test tube method composed of a bottom reagent phase, a middle fluorous phase, and a top substrate phase. In such a triphasic system, the fluorous phase acts as a liquid membrane to transport the bottom reagents to the top organic phase containing substrates. In the end, the bottom layer disappears and two phases remain. Since the first demonstration of the PV method by bromination of alkenes with molecular bromine, a number of applications have been developed thus far. These include halogenation of alcohols with SOBr(2) and PBr(3), demethylation of methoxyarenes with BBr(3), cyclopropanation of alkenes by CH(2)I(2)-AlEt(3), and Friedel-Crafts acylation of aromatic compounds with SnCl(4). A fluorous triphasic U-tube method is effective for chlorination of alcohols based on lighter (less dense) reagents such as SOCl(2) and PCl(3). A system using a solution containing reagents as a bottom phase is useful for oxidation with m-CPBA, which may be defined as a new category for the "extractive PV" method. Recent advances include a "quadraphasic" PV method, in which an aqueous "scavenger" phase is added to the original triphasic PV method to remove acidic by-products.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:issn
1528-0691
pubmed:author
pubmed:copyrightInfo
2008 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.
pubmed:issnType
Electronic
pubmed:volume
8
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
351-63
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Phase-vanishing methods based on fluorous phase screen: a simple way for efficient execution of organic synthesis.
pubmed:affiliation
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan. ryu@c.s.osakafu-u.ac.jp
pubmed:publicationType
Journal Article, Review, Research Support, Non-U.S. Gov't, Research Support, N.I.H., Extramural