1,2,4-Oxadiazole 4-Oxides as Nitrones in 1,3-Dipolar Cycloaddition Reactions to Vinyl Ethers

被引：5

作者：

Quadrelli, Paolo ^{[1
]}

Lunghi, Fabio ^{[1
]}

Bovio, Bruna ^{[1
]}

Gautschi, William ^{[1
]}

Caramella, Pierluigi ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim, I-27100 Pavia, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 07期

关键词：

Heterocycles; Nitrones; Vinyl ethers; Cycloaddition; Synthesis design; HETERO-DIELS-ALDER; HETEROAROMATIC AMINE OXIDES; NITRILE OXIDES; ENE REACTIONS; PHOTOCHEMICAL GENERATION; NITROSOCARBONYL; CYCLITOLS;

D O I：

10.1002/ejoc.201101615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2,4-Oxadiazole 4-oxides display nitronic reactivity and selectivities identical to those of N-methyl-C-phenyl nitrone, which is a typical acyclic nitrone, affording comparable amounts of endo- and exo-5-alkoxyisoxazolidines. The exo stereoisomers undergo an easy rearrangement under the reaction conditions to yield oxadiazolinic esters. The structures of the adducts have been confirmed by X-ray structures and spectroscopic data. A donor p-methoxyphenyl at the nitronic carbon slows down the cycloaddition rate, while an acceptor p-nitrophenyl retards the rearrangement of the exo adduct.

引用

页码：1418 / 1425

页数：8

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