9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles

V. D. Filimonov, S. G. Gorbachev, E. E. Sirotkina

Research output: Contribution to journalArticle

Abstract

A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.

Original languageEnglish
Pages (from-to)252-255
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume16
Issue number3
DOIs
Publication statusPublished - 1 Mar 1980

Fingerprint

Isomers
Isomerization
Dimethyl Sulfoxide
Ultraviolet spectroscopy
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
carbazole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles. / Filimonov, V. D.; Gorbachev, S. G.; Sirotkina, E. E.

In: Chemistry of Heterocyclic Compounds, Vol. 16, No. 3, 01.03.1980, p. 252-255.

Research output: Contribution to journalArticle

Filimonov, V. D. ; Gorbachev, S. G. ; Sirotkina, E. E. / 9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles. In: Chemistry of Heterocyclic Compounds. 1980 ; Vol. 16, No. 3. pp. 252-255.
@article{0b03ce2fb8d14075bc19905474564ab4,
title = "9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles",
abstract = "A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.",
author = "Filimonov, {V. D.} and Gorbachev, {S. G.} and Sirotkina, {E. E.}",
year = "1980",
month = "3",
day = "1",
doi = "10.1007/BF02401721",
language = "English",
volume = "16",
pages = "252--255",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "3",

}

TY - JOUR

T1 - 9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles

AU - Filimonov, V. D.

AU - Gorbachev, S. G.

AU - Sirotkina, E. E.

PY - 1980/3/1

Y1 - 1980/3/1

N2 - A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.

AB - A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.

UR - http://www.scopus.com/inward/record.url?scp=34250254603&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34250254603&partnerID=8YFLogxK

U2 - 10.1007/BF02401721

DO - 10.1007/BF02401721

M3 - Article

VL - 16

SP - 252

EP - 255

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 3

ER -