9-Alkenylcarbazoles. 7. Regiospecific and stereospecific addition of carbazole and indole to phenylacetylene. Structure and some properties of cis-9-(2-phenylvinyl)carbazole

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Abstract

Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole. A cis-phenyl group markedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom. It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays π-donor properties with respect to the styryl group.

Original languageEnglish
Pages (from-to)148-151
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume17
Issue number2
DOIs
Publication statusPublished - Feb 1981

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Protonation
Dimethyl Sulfoxide
Ultraviolet spectroscopy
Isomers
Nuclear magnetic resonance spectroscopy
Hydrolysis
Display devices
Atoms
Acids
indole
carbazole
phenylacetylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "9-Alkenylcarbazoles. 7. Regiospecific and stereospecific addition of carbazole and indole to phenylacetylene. Structure and some properties of cis-9-(2-phenylvinyl)carbazole",
abstract = "Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole. A cis-phenyl group markedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom. It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays π-donor properties with respect to the styryl group.",
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T1 - 9-Alkenylcarbazoles. 7. Regiospecific and stereospecific addition of carbazole and indole to phenylacetylene. Structure and some properties of cis-9-(2-phenylvinyl)carbazole

AU - Filimonov, V. D.

PY - 1981/2

Y1 - 1981/2

N2 - Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole. A cis-phenyl group markedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom. It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays π-donor properties with respect to the styryl group.

AB - Under the influence of strong bases in dimethyl sulfoxide (DMSO) under mild conditions, carbazole and indole add smoothly to phenylacetylene to give cis isomers of 9-(2-phenylvinyl)carbazole and 1-(2-phenylvinyl)indole. A cis-phenyl group markedly reduces the activity of the double bond of phenylvinylcarbazole in acid hydrolysis, but, as in the case of other alkenylcarbazoles, protonation takes place at the vinyl Cβ atom. It was established by 13C NMR and UV spectroscopy that the carbazolyl group displays π-donor properties with respect to the styryl group.

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