Linked Life Data

20572186

Source:http://linkedlifedata.com/resource/pubmed/id/20572186

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
29
pubmed:dateCreated
2010-8-3
pubmed:abstractText
Exposure of sulfides and sulfoxides to trifluoromethanesulfonylimino(aryl)-lambda(3)-bromane in dichloromethane at 0 degrees C results in a facile transfer of the sulfonylimino group to sulfur atoms and affords N-triflylsulfilimines and -sulfoximines in high yields under transition-metal-free conditions. Imination of (R)-methyl p-tolyl sulfoxide proceeded with predominant retention of configuration at the stereogenic sulfur center. The Hammett plot afforded rho values of -0.58 for para-substituted thioanisoles and -0.49 for their equivalent sulfoxides, which suggests a buildup of positive charge on the sulfur atoms of sulfides and sulfoxides in the transition state. Calculations suggest a bimolecular nucleophilic-substitution mechanism on the negatively charged nitrogen atom of the sulfonylimino-lambda(3)-bromane, which involves the attack of a sulfide from the opposite side to bromine(III).
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Aug
pubmed:issn
1521-3765
pubmed:author
pubmed:issnType
Electronic
pubmed:day
2
pubmed:volume
16
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
8713-8
pubmed:meshHeading
pubmed:year
2010
pubmed:articleTitle
Imination of sulfides and sulfoxides with sulfonylimino-lambda3-bromane under mild, metal-free conditions.
pubmed:affiliation
Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't