Diels-alder reaction of 1-methylcycloprop-2-ene-1-carbonitrile with methyl 2-oxo-2H-pyran-5-carboxylate |
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| Authors: | V V Plemenkov R V Ashirov O A Lodochnikova I A Litvinov R N Zagidullin |
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| Institution: | (1) Kazan State Medical University, ul. Butlerova 49, Kazan, 420012, Tatarstan, Russia;(2) Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia |
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| Abstract: | 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. |
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