New, simple and selective synthesis of perfluoroalkylquinones by perfluoroalkyl radicals - Enthalpic and polar effects

被引：12

作者：

Antonietti, F ^{[1
]}

Gambarotti, C ^{[1
]}

Mele, A ^{[1
]}

Minisci, F ^{[1
]}

Paganelli, R ^{[1
]}

Punta, C ^{[1
]}

Recupero, F ^{[1
]}

机构：

[1] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20131 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 20期

关键词：

perfluoroalkyl radicals; quinones; captodative effect; polar effect; enthalpic effect;

D O I：

10.1002/ejoc.200500314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Perfluoroalkyl radicals (R-f), generated by iodine abstraction from perfluoroalkyl iodides by phenyl radicals, react selectively with quinone rings in spite of their electrophilic character. In the presence of electron-rich alkenes, R-f adds faster to the electron-rich double bonds forming a radical adduct with reversed polar effect, which selectively adds to quinone. The mechanism of the reactions involved are discussed, emphasizing the key role of enthalpic and polar effects and the particular reactivity of 2-methoxynaphthoquinone due to polar and captodative effects. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

引用

页码：4434 / 4440

页数：7

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