Diels—Alder Reaction of 1-Methylcycloprop-2-ene-1-carbonitrile with Methyl 2-Oxo-2H-pyran-5-carboxylate

Autor:	R. N. Zagidullin, V. V. Plemenkov, R. V. Ashirov, Igor A. Litvinov, Olga A. Lodochnikova
Rok vydání:	2006
Předmět:	Stereochemistry Organic Chemistry Cycloheptatriene General Medicine Medicinal chemistry Adduct Cyclopropane chemistry.chemical_compound chemistry Pyran Carboxylate Isomerization Ene reaction Diels–Alder reaction
Zdroj:	ChemInform. 37
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200650079
Popis:	The Diels-Alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile and coumalic acid methyl ester (methyl 2-oxo-2H-pyran-5-carboxylate) gave a 2:1 adduct with endo-syn configuration of both cyclopropane fragments, which was established by X-ray analysis. According to the 1H NMR data, the reaction involves intermediate formation of decarboxylated 1:1 adduct having a cycloheptatriene structure; its isomerization into the corresponding caradiene, followed by addition of the second dienophile molecule, was confirmed by quantum-chemical calculations.
Databáze:	OpenAIRE
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