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Chiral-optical properties of six- and seven-membered benzothioamides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The chiral-optical properties of R-(+)-4-methyl-3,4-di-hydroisoquinoline-1-thione and R-(-)-3-methyl-, R-(+)-4-methyl-, and S-(+)-5-methyl-2,3,4,5-tetrahydrobenz[c]-azepine-1-thiones were studied. A significant increase in the intensities of the Cotton effects (CE), particularly for the CE due to the n → π* transition in the benzothioamide chromophore, is observed on passing from six-membered to seven-membered benzothiolactams with the same orientation of the asymmetric center relative to the chromophore. The signs of the CE due to the n → π* transition in the benzothioamide chromophore and the π → π* transition in the aromatic chromophore at 250–280 nm (the 1Lb band) correlate with the type of conformation of the thiolactam ring.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 119899, Moscow

    V. M. Potapov, V. M. Dem'yanovich, L. D. Solov'eva & O. E. Vendrova

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  1. V. M. Potapov
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  2. V. M. Dem'yanovich
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  3. L. D. Solov'eva
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  4. O. E. Vendrova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1233–1237, September, 1985.

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Potapov, V.M., Dem'yanovich, V.M., Solov'eva, L.D. et al. Chiral-optical properties of six- and seven-membered benzothioamides. Chem Heterocycl Compd 21, 1026–1030 (1985). https://doi.org/10.1007/BF00515029

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  • DOI: https://doi.org/10.1007/BF00515029

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