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4-Dimethylaminoacetophenone O-vinyloxime: Synthesis and steric structure

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Abstract

4-Dimethylaminoacetophenone oxime was synthesized from 4-dimethylaminoacetophenone and hydroxylamine hydrochloride. Its reaction with acetylene in the system KOH-DMSO gave previously unknown 4-dimethylaminoacetophenone O-vinyloxime as the major product. According to the experimental data and quantum-chemical calculations, 4-dimethylaminoacetophenone O-vinyloxime is formed as the only E isomer with preferential s-trans conformation of the vinyloxy group, which is characterized by essentially nonplanar structure.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    L. N. Sobenina, A. P. Demenev, A. I. Mikhaleva, Yu. Yu. Rusakov, L. I. Larina, N. V. Istomina & L. B. Krivdin

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  1. L. N. Sobenina
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  2. A. P. Demenev
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  3. A. I. Mikhaleva
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  4. Yu. Yu. Rusakov
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  5. L. I. Larina
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  6. N. V. Istomina
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  7. L. B. Krivdin
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Correspondence to L. N. Sobenina.

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Dedicated to Full Member of the Russian Academy of Sciences B.A. Trofimov on his 70th anniversary

Original Russian Text © L.N. Sobenina, A.P. Demenev, A.I. Mikhaleva, Yu.Yu. Rusakov, L.I. Larina, N.V. Istomina, L.B. Krivdin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 10, pp. 1521–1526.

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Sobenina, L.N., Demenev, A.P., Mikhaleva, A.I. et al. 4-Dimethylaminoacetophenone O-vinyloxime: Synthesis and steric structure. Russ J Org Chem 44, 1497–1503 (2008). https://doi.org/10.1134/S1070428008100163

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  • DOI: https://doi.org/10.1134/S1070428008100163

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