Synthesis of [2.2]paracyclophane-pseudo-ortho-dicarboxylic acid

被引：10

作者：

Antonov, DY ^{[1
]}

Sergeeva, EV ^{[1
]}

Vorontsov, EV ^{[1
]}

Rozenberg, VI ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 1997年 / 46卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

2.2]paracyclophane; 2.2]paracyclophane-pseudo-ortho-dicarboxylic acid; lithiation; carboxylation;

D O I：

10.1007/BF02503781

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient three-step synthesis of [2.2]paracyclophane-pseudo-ortho-dicarboxylic acid by dibromination of [2.2]paracyclophane, thermal isomerization of the resulting pseudo-para-dibromide to pseudo-ortho-isomer, followed by lithiation/carboxylation was developed. The possibility of preparation of two other novel pseudo-ortho-disubstituted carbonyl derivatives, 4-carboxy-12-(1-oxopenthyl)-[2.2]paracyclophane and di(4-carboxy[2.2]paracyclophanyl-12)ketone, was demonstrated when an excess of lithiation reagent (4 or 10 eq.) was used in the final step.

引用

页码：1897 / 1900

页数：4

共 13 条

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REICH, HJ ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (13) :3517-&

[12] MACRO RINGS .37. MULTIPLE ELECTROPHILIC SUBSTITUTION REACTIONS OF [2.2]PARACYCLOPHANES AND INTERCONVERSIONS OF POLYSUBSTITUTED DERIVATIVES [J].

REICH, HJ ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (13) :3527-&

[13]

YEH JL, 1969, J ORG CHEM, V34, P2366

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