| One-pot regioselective synthesis of nitrophenyloxazolinyl styrene oxides by the Darzens reaction of vicarious nucleophilic substitution-formed carbanions of 2-dichloromethyl-4,4-dimethyloxazoline. | |
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MedLine Citation:
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PMID: 15255722 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Saverio Florio; Patrizia Lorusso; Catia Granito; Renzo Luisi; Luigino Troisi |
Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Jul |
Date Detail:
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Created Date: 2004-07-16 Completed Date: 2004-09-17 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4961-5 Citation Subset: - |
Affiliation:
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Dipartimento Farmaco-Chimico, University of Bari, Via E. Orabona 4, I-70126 Bari, Italy. florio@farmchim.uniba.it |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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