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Synthesis and reactions of N-acetyl- and N-(2-chloroacetyl)-N-[(2E)-1-methylbut-2-en-1-yl]-2-iodoanilines

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Abstract

The reaction of N-(1-methylbut-2-en-1-yl)-2-iodaniline with Ac2O or ClCH2C(O)Cl results in a mixture of syn- and anti-atropisomers of N-acetyl- and N-chloroacetyl-N-(1-methylbut-2-en-1-yl)-2-iodaniline in a ratio of 1:1. Ozonolysis of the latter followed by reduction with dimethyl sulfide in CH2Cl2 gives rise to the atropisomers mixture of 2-[N-(chloroacetyl)-N-(2-iodophenyl)]aminopropanal in a ratio of 1:3. When heated in boiling benzene, the mixture of atropoisomeric aldehydes reacts with triphenylphosphine to afford a mixture of 2-[(N-acetyl)-N-(2-iodophenyl)]aminopropanal atropisomers in 1:3 ratio.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Russia

    D. A. Skladchikov & R. R. Gataullin

Authors
  1. D. A. Skladchikov
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  2. R. R. Gataullin
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Correspondence to R. R. Gataullin.

Additional information

Original Russian Text © D.A. Skladchikov, R.R. Gataullin, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 2, pp. 313–317.

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Skladchikov, D.A., Gataullin, R.R. Synthesis and reactions of N-acetyl- and N-(2-chloroacetyl)-N-[(2E)-1-methylbut-2-en-1-yl]-2-iodoanilines. Russ J Gen Chem 83, 368–372 (2013). https://doi.org/10.1134/S1070363213020217

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  • DOI: https://doi.org/10.1134/S1070363213020217

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