Please use this identifier to cite or link to this item:
|Type:||Artigo de periódico|
|Title:||Electronically mediated selectivity in ring opening of 1-azirines. The 3-X mode: Convenient route to 3-oxazolines|
|Abstract:||The mild base-promoted reaction of methyl 2-phenyl-1-azirine-3-acetate (1) with aldehydes and acetone provides a new and simple route to the 3-oxazolines 5, which are formed in good yields by the electrophilic trapping of an imino anion produced by C-N bond cleavage in the 1-azirine enolate intermediate 6. Chloranil oxidation of 5 containing an aromatic substituent at C-2 affords oxazoles 7, while reaction of 5 containing an aliphatic group at C-2 produces 5-methylene-3-oxazolines 8 and 5-spiro-2-oxazolines 9 in addition to 7.|
|Editor:||Amer Chemical Soc|
|Citation:||Journal Of Organic Chemistry. Amer Chemical Soc, v. 61, n. 11, n. 3749, n. 3752, 1996.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.