Synthesis of Dibenz[b,f]oxepins via Manganese(III)-Based Oxidative 1,2-Radical Rearrangement

被引：49

作者：

Cong, Zhiqi ^{[1
]}

Miki, Takumi ^{[1
]}

Urakawa, Osamu ^{[1
]}

Nishino, Hiroshi ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Sci & Technol, Dept Chem, Kurokami 2-39-1, Kumamoto 8608555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 10期

基金：

日本学术振兴会;

关键词：

FREE-RADICAL REACTIONS; 1,3-DICARBONYL COMPOUNDS; AROMATIC-COMPOUNDS; VALENCE TAUTOMER; ACETATE; DERIVATIVES; CYCLIZATION; ACIDS; 2-AMINO-1,4-NAPHTHOQUINONES; 2-AMINO-1,4-BENZOQUINONES;

D O I：

10.1021/jo9002773

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The oxidation of monoalkyl 2-(9H-xanthenyl)malonates 1 with Mn(OAc)(3) gave the 9- or 10-dibenz[b,f]oxepincarboxylates 2 in good yields. The reaction proceeds with high regioselectivity except for the case of (1-methoxyxanthenyl)malonate 1 (R-1 = Me, R-2 = 1-MeO), which gave two regioisomers. It was proposed that the process for the formation of 2 must include the 1,2-aryl radical rearrangement followed by oxidative decarboxylation.

引用

页码：3978 / 3981

页数：4

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