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

Salikov Rinat F. | Zendy; Trainov Konstantin P. | Zendy; Platonov Dmitry N. | Zendy; Belyy Alexander Yu. | Zendy; Tomilov Yury V. | Zendy

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

Author(s) -

Salikov Rinat F.,

Trainov Konstantin P.,

Platonov Dmitry N.,

Belyy Alexander Yu.,

Tomilov Yury V.

Publication year - 2018

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201800732

Subject(s) - chemistry , dimethyl acetylenedicarboxylate , sodium borohydride , cycloaddition , pyridine , electrocyclic reaction , pyridinium , medicinal chemistry , ring (chemistry) , stereochemistry , organic chemistry , catalysis

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.

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