1,3-Dipolar cycloaddition of nitrile oxides with C1-substituted 7-oxabenzonorbornadienes

Autor:	R NagireddyJaipal, TamWilliam, CarlsonEmily
Rok vydání:	2014
Předmět:	7-oxabenzonorbornadiene Nitrile Organic Chemistry Oxide Regioselectivity General Chemistry Catalysis Benzonitrile chemistry.chemical_compound chemistry Acetonitrile oxide 1 3-Dipolar cycloaddition Polymer chemistry Organic chemistry
Zdroj:	Canadian Journal of Chemistry. 92:1053-1058
ISSN:	1480-3291 0008-4042
DOI:	10.1139/cjc-2014-0274
Popis:	1,3-Dipolar cycloadditions of unsymmetrical C1-substituted 7-oxabenzonorbornadienes with acetonitrile oxide and benzonitrile oxide were investigated to probe the regio- and stereoselectivities of these reactions. All novel oxabicycle-fused isoxazoline adducts were obtained in moderate to excellent yields (53%–98%) and with complete exo-stereoselectivity. The major regioisomer in almost all instances showed positioning of the nitrile oxide’s methyl or phenyl group anti to the C1-substituent. The relative ratios of the regioisomers suggested nonnegligible electronic and steric contributions of the C1-substituent in these reactions. Several useful applications of these 2-isoxazolines toward natural product synthesis are proposed via reductive cleavage of their N–O bonds.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dbf4e2cd3b1ae5a48d1382b7bc9f2b65 https://doi.org/10.1139/cjc-2014-0274 Zobrazit plný text záznamu Plný text ve formátu PDF