Unusual Side Transformation of Spiro[2,4]hepta‐4,6‐dienes into Fulvene Derivatives During Pd‐Catalyzed Cyclopropanation with Diazomethane

Unusual Side Transformation of Spiro[2,4]hepta‐4,6‐dienes into Fulvene Derivatives During Pd‐Catalyzed Cyclopropanation with Diazomethane Научная публикация

Журнал

ChemistrySelect
ISSN: 2365-6549

Вых. Данные

Год: 2020, Том: 5, Номер: 13, Страницы: 4046-4049 Страниц : 4 DOI: 10.1002/slct.202000160

Авторы

Shulishov Evgeny V. ¹ , Pantyukh Olga A. ¹ , Menchikov Leonid G. ¹ , Tomilov Yury V. ¹

Организации

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

The catalytic cyclopropanation of spiro[2.4]hepta-4,6-diene and 1,1,2,2-tetradeutero-, 1-methyl-, and 1,1-dimethylspiro[2.4]hepta-4,6-dienes on treatment with excess diazomethane in the presence of palladium catalysts, which gives products of double bond dicyclopropanation, is also accompanied by an unusual transformation of the three-membered ring of the spiro moiety with elimination of the unsubstituted methylene group in the form of ethylene to give the corresponding 5-methylidenetricyclo[4.1.0.02,4]heptanes (bishomofulvenes). The putative mechanism of the reactions is considered.

Shulishov E.V. , Pantyukh O.A. , Menchikov L.G. , Tomilov Y.V.
Unusual Side Transformation of Spiro[2,4]hepta‐4,6‐dienes into Fulvene Derivatives During Pd‐Catalyzed Cyclopropanation with Diazomethane
ChemistrySelect. 2020. V.5. N13. P.4046-4049. DOI: 10.1002/slct.202000160 WOS Scopus OpenAlex

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