Unusual manganese(III)-mediated oxidative free-radical additions of Meldrum's acid and dimethyl malonate to benzonorbornadiene and oxabenzonorbornadiene

被引：10

作者：

Caliskan, Rasit ^{[1
]}

Nohut, Neslihan ^{[1
]}

Yilimaz, Ozlem ^{[1
]}

Sahin, Ertan ^{[2
]}

Balci, Metin ^{[3
]}

机构：

[1] Suleyman Demirel Univ, Dept Chem, TR-32260 Isparta, Turkey

[2] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey

[3] Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey

来源：

TETRAHEDRON | 2017年 / 73卷 / 04期

关键词：

Manganase(III) acetate; Copper(II) acetate; Cycloaddition; Oxidation; Dihydrofurans; Rearrangement; Benzonorbornadiene; Oxabenzonorbornadiene; 1,3-DICARBONYL COMPOUNDS; METAL-SALTS; ACETATE; CYCLIZATIONS; DIHYDROFURANS; DERIVATIVES; MECHANISMS; MN(OAC)(3); ALKENES; KETONES;

D O I：

10.1016/j.tet.2016.11.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzonorbornadiene and 7-oxabenzonorbornadiene were reacted with Meldrum's acid and dimethyl malonate in the presence of Mn(OAc)(3) and Cu(OAc)(2) in acetic acid. The reaction of benzonorbornadiene with Meldrum's acid gave a naphthalene derivative whereas the reaction with dimethyl malonate formed rearranged products derived from a carbocation intermediate. However, the reaction of 7-oxabenzonorbornadiene with Meldrum's acid gave two nonrearranged products. On the other hand, the reaction with dimethyl malonate unexpectedly formed a dihydronapthalene derivative with an unusual structure. The mechanism for the formation of the products is discussed. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：291 / 297

页数：7

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