Abstract
The1H and13C NMR spectra of 9-vinylcarbazole and its 3-chloro, 3,6-dichloro, and 3-nitro derivatives were recorded and studied. It is shown that electron-acceptor substituents reduce the shielding of the β-carbon atom and the trans proton of the vinyl group. A good linear correlation between the chemical shifts of these nuclei and the Hammettσ −para constants with theρ values (3.78 for13Cβ and 0.28 for1Htrans) is observed. It was established by comparison of the results with the1H and13C NMR spectral parameters for some of the vinyl compounds that the degree of conjugation of the p electrons of nitrogen with theπ electrons of the double bond in 9-vinylcarbazoles is lower than in simple vinyl and vinyl phenyl ethers and vinyl acetate.
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See [25] for communication I.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1368–1371, October, 1976.
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Filimonov, V.D., Anfinogenov, V.A. & Matyukov, N.E. 9-alkenylcarbazoles. Chem Heterocycl Compd 12, 1133–1136 (1976). https://doi.org/10.1007/BF00945599
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DOI: https://doi.org/10.1007/BF00945599