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Henry condensation under high pressure 2. Effect of aromatic aldehyde type and pressure on the yield of ω-nitrostyrenes and secondary processes

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarilyω-nitrostyrenes (Ia, b)-(XXa, b) and small quantities of nitriles (Ic)-(XXc), oximes (Id)-(XXd), and ketones (Ie, f)-(XXe, f). The yields of (Ia, b)-(XXa, b) at P=1 atm are higher for acceptor substituents on the aromatic ring whereas at P=10 kbar, they are higher for donor substituents. High pressures suppress the formation of (Ic-f)-(XXc-f) and the Z-isomers of (Ia, b)-(XXa, b). The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b)-(XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    N. E. Agafonov, I. P. Sedishev, A. V. Dudin, A. A. Kutin, G. A. Stashina & V. M. Zhulin

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  1. N. E. Agafonov
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  2. I. P. Sedishev
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  3. A. V. Dudin
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  4. A. A. Kutin
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  5. G. A. Stashina
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  6. V. M. Zhulin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 426–433, February, 1991.

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Agafonov, N.E., Sedishev, I.P., Dudin, A.V. et al. Henry condensation under high pressure 2. Effect of aromatic aldehyde type and pressure on the yield of ω-nitrostyrenes and secondary processes. Russ Chem Bull 40, 366–372 (1991). https://doi.org/10.1007/BF00965433

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  • DOI: https://doi.org/10.1007/BF00965433

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