Document Detail


One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline.
MedLine Citation:
PMID:  15255722     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The vicarious nucleophilic substitution reaction of dichloromethyloxazoline 2 with nitrobenzene has been investigated. Treatment of 2 with t-BuOK followed by the addition of nitrobenzene leads to benzylic carbanions 4 or 9 depending upon the solvent used (DMSO, DMF, or THF). Subsequent treatment of 4 or 9 with aldehydes, in a Darzens-like reaction, furnishes very good yields of nitrophenyl oxazolinyloxiranes 8 and 11. 1,2-Dioxazolinyl-1,2-dinitrophenylethene 7 forms quantitatively when carbanion 4 is allowed to warm to room temperature in the absence of external electrophiles.
Authors:
Saverio Florio; Patrizia Lorusso; Catia Granito; Renzo Luisi; Luigino Troisi
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Jul 
Date Detail:
Created Date:  2004-07-16     Completed Date:  2004-09-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4961-5     Citation Subset:  -    
Affiliation:
Dipartimento Farmaco-Chimico, University of Bari, Via E. Orabona 4, I-70126 Bari, Italy. florio@farmchim.uniba.it
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Phototransposition reactions of arylboronate esters in acetonitrile and 2,2,2-trifluoroethanol.
Next Document:  Stereoselectivity and regioselectivity in nucleophilic ring opening in derivatives of 3-phenylisoxaz...