Abstract
According to 1H and 13C NMR, the vinyl group in 10-vinylphenothiazine is coplanar with the plane orthogonal to the axis of the lone pair on nitrogen, as a result of bending of the ring along the S-N axis. In 10-vinylphenothiazine S-oxide, this bending does not occur, and as a result of the steric influence of the heterocycle the vinyl group is located nearly orthogonally to the heterocycle, and is analogous to the spatial structure of 10-vinylacridone. In 9-vinylcarbazole, the N-Cα torsion angle is 60°, increasing to 75° in 9-vinyl-1-methyl-β-carboline.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 408–415, March, 1992.
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Afonin, A.V., Kurov, G.N., Dmitriev, L.L. et al. Structural examination of 1-vinylphenothiazine, 10-vinylphenothiazine S-oxide, 10-vinylcarbazole, 9-vinylcarbazole, and 9-vinyl-β-carboline by 1H and 13C NMR. Chem Heterocycl Compd 28, 344–349 (1992). https://doi.org/10.1007/BF00529384
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DOI: https://doi.org/10.1007/BF00529384