Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)-diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons

被引：71

作者：

Zhang, Hongyu ^{[1
]}

Karasawa, Takashi ^{[1
]}

Yamada, Hiroshi ^{[1
]}

Wakamiya, Atsushi ^{[1
]}

Yamaguchi, Shigehiro ^{[1
]}

机构：

[1] Nagoya Univ, Dept Chem, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 14期

关键词：

5-ENDO-DIG CYCLIZATION; SILICON; DERIVATIVES; CARBOALKOXYLATION; CONSTRUCTION; HETEROCYCLES; STILBENES; ALKYNES;

D O I：

10.1021/ol901148p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Upon the treatment of bis(arylcarbonyl)diphenylacetylenes with lithium naphthalenide, the carbonyl reduction dominantly occurs over the acetylene reduction. The produced bis(radical anion) intermediate undergoes a synchronous double-radical 5-endo-dig cyclization. This simple reduction procedure produces two intriguing classes of ladder pi-conjugated skeletons, i.e., emissive methylene-bridged stilbenes and dibenzo[a,e]pentalenes regarded as a cyclic 1,4-diphenylbutadiene.

引用

页码：3076 / 3079

页数：4

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