Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions

被引：8

作者：

Salikov, Rinat F. ^{[1
]}

Trainov, Konstantin P. ^{[1
]}

Platonov, Dmitry N. ^{[1
]}

Belyy, Alexander Yu. ^{[1
]}

Tomilov, Yury V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prospect, Moscow 119991, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 36期

关键词：

Electrocyclic reactions; Ring contraction; Bronsted acids; Reaction mechanisms; BRONSTED ACID; COMPLEXES; CRYSTAL; PENTAKIS(METHOXYCARBONYL)CYCLOPENTADIENE; POTASSIUM; RUTHENIUM; CHEMISTRY;

D O I：

10.1002/ejoc.201800732

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism for the reaction of dimethyl malonate with dimethyl acetylenedicarboxylate in the presence of pyridine and acetic acid to form isomeric octa(methoxycarbonyl)cycloheptadienes was established. The formation of intermediary N-[di(methoxycarbonyl)vinyl]pyridinium acetate was proven by means of NMR spectroscopy. On the basis of the established mechanism, dimethyl dibromosuccinate was proposed to be used instead of dimethyl acetylenedicarboxylate. A novel method for the synthesis of penta(methoxycarbonyl)cyclopentadienylsodium through the reduction of hepta(methoxycarbonyl)cycloheptatriene with sodium borohydride, electrocyclic ring contraction and retro-[2+2]-cycloaddition was developed.

引用

页码：5065 / 5068

页数：4

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