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STEREOCHEMISTRY OF PHOTOCYCLOADDITION PRODUCTS OF ACENAPHTHYLENE WITH ACRYLONITRILE AND METHYL ACRYLATE

Y. Nakamura, Yasuhiro Imakura, Yutaka Morita

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Abstract

Abstract Stereochemistry of photocycloaddition products of acenaphthylene with acrylonitrile and methyl acrylate were decided by the chemical transformations and the NMR spectral correlation with those of their derivatives, viz., equilibriation of the deuterated isomers of acrylonitrile-adduct with t-BuOK/BuOD, reduction to amine with LiAlH4, acetylation of amine, and hydrolysis followed by methylation of acrylonitrile-adduct to methyl acrylate adduct.

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Abstract Stereochemistry of photocycloaddition products of acenaphthylene with acrylonitrile and methyl acrylate were decided by the chemical transformations and the NMR spectral correlation with those of their derivatives, viz., equilibriation of the deuterated isomers of acrylonitrile-adduct with t-BuOK/BuOD, reduction to amine with LiAlH4, acetylation of amine, and hydrolysis followed by methylation of acrylonitrile-adduct to methyl acrylate adduct.

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Available abstract

Abstract Stereochemistry of photocycloaddition products of acenaphthylene with acrylonitrile and methyl acrylate were decided by the chemical transformations and the NMR spectral correlation with those of their derivatives, viz., equilibriation of the deuterated isomers of acrylonitrile-adduct with t-BuOK/BuOD, reduction to amine with LiAlH4, acetylation of amine, and hydrolysis followed by methylation of acrylonitrile-adduct to methyl acrylate adduct.

Key concepts: Acrylonitrile, Chemistry, Acenaphthylene, Methyl acrylate, Adduct, Amine gas treating, Hydrolysis, Acrylate

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STEREOCHEMISTRY OF PHOTOCYCLOADDITION PRODUCTS OF ACENAPHTHYLENE WITH ACRYLONITRILE AND METHYL ACRYLATE — Research Paper | ScholarLens