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

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

Журнал

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Вых. Данные

Год: 2018, Том: 2018, Номер: 36, Страницы: 5065-5068 Страниц : 4 DOI: 10.1002/ejoc.201800732

Авторы

Salikov Rinat F. ¹ , Trainov Konstantin P. ¹ , Platonov Dmitry N. ¹ , Belyy Alexander Yu. ¹ , Tomilov Yury V. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, 119991 Moscow, Russian Federation

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.

Salikov R.F. , Trainov K.P. , Platonov D.N. , Belyy A.Y. , Tomilov Y.V.
Synthesis of 1,2,3,4,5‐Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions
European Journal of Organic Chemistry. 2018. V.2018. N36. P.5065-5068. DOI: 10.1002/ejoc.201800732 WOS Scopus OpenAlex

≡ Web of science:	WOS:000445850800012
≡ Scopus:	2-s2.0-85052520579
≡ OpenAlex:	W2806231511