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Title: Phosphorus-containing enamines. IV. Reactions of alkyl- and phenyl-substituted 1-vinylpyrroles with phosphorus pentachloride

Abstract

1-Vinylpyrroles, alkyl- and phenyl-substituted in the ring, are phosphorylated by phosphorus pentachloride in the ..cap alpha.. position of the pyrrole ring with the subsequent addition of the chlorophosphorane at the N-vinyl group with the formation of pyrrolo(1,2-a)-1,1,3-trichloro-4,1-azaphospholanium hexachlorophosphates. By treating the phosphorylation products with sulfur dioxide and triethylamine the authors synthesized pyrrolo(1,2-a)-1-oxo-1-chloro-4,1-azaphosphol-2-enes. The introduction of phenyl substituents into the nucleus of 1-vinylpyrroles or of alkyl substituents in the C/sup 2/ and C/sup 5/ positions is conducive to substitutive phosphorylation in the vinyl group and the formation of phosphorus-containing enamines. 1-Vinylindole and 9-vinylcarbazole are phosphorylated exclusively at the vinyl group. Hydrogen 1, phosphorus 32, and carbon 13 NMR spectra are analyzed in detail.

Authors:
; ; ; ; ; ;
Publication Date:
Research Org.:
A. A. Zhdanov Irkut-sk State Univ. (USSR)
OSTI Identifier:
5416697
Resource Type:
Journal Article
Journal Name:
J. Gen. Chem. USSR (Engl. Transl.); (United States)
Additional Journal Information:
Journal Volume: 56:4; Other Information: Translated from Zh. Obshch. Khim.; 56: No. 4, 790-804(Apr 1986)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS; AMINES; HYPERFINE STRUCTURE; NMR SPECTRA; ORGANIC PHOSPHORUS COMPOUNDS; PYRROLES; CHLORINATION; PHOSPHORYLATION; CARBAZOLES; CARBON 13; CHEMICAL SHIFT; CHLOROFORM; COUPLING CONSTANTS; ELECTRON DENSITY; ELECTRONIC STRUCTURE; HYDROGEN 1; INDOLES; INFRARED SPECTRA; J-J COUPLING; MOLECULAR STRUCTURE; MULTIPLETS; ORGANIC CHLORINE COMPOUNDS; PHOSPHORUS 31; PHOSPHORUS CHLORIDES; SULFUR DIOXIDE; SYNTHESIS; AROMATICS; AZAARENES; AZOLES; CARBON ISOTOPES; CHALCOGENIDES; CHEMICAL REACTIONS; CHLORIDES; CHLORINATED ALIPHATIC HYDROCARBONS; CHLORINE COMPOUNDS; COUPLING; EVEN-ODD NUCLEI; HALIDES; HALOGEN COMPOUNDS; HALOGENATED ALIPHATIC HYDROCARBONS; HALOGENATION; HETEROCYCLIC COMPOUNDS; HYDROGEN ISOTOPES; INTERMEDIATE COUPLING; ISOTOPES; LIGHT NUCLEI; NUCLEI; ODD-EVEN NUCLEI; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; OXIDES; OXYGEN COMPOUNDS; PHOSPHORUS COMPOUNDS; PHOSPHORUS ISOTOPES; SPECTRA; STABLE ISOTOPES; SULFUR COMPOUNDS; SULFUR OXIDES; 400201* - Chemical & Physicochemical Properties; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory

Citation Formats

Rozinov, V G, Pensionerova, G A, Donskikh, V I, Sergienko, L M, Korostova, S E, Nikhaleva, A I, and Dolgushin, G V. Phosphorus-containing enamines. IV. Reactions of alkyl- and phenyl-substituted 1-vinylpyrroles with phosphorus pentachloride. United States: N. p., 1986. Web.
Rozinov, V G, Pensionerova, G A, Donskikh, V I, Sergienko, L M, Korostova, S E, Nikhaleva, A I, & Dolgushin, G V. Phosphorus-containing enamines. IV. Reactions of alkyl- and phenyl-substituted 1-vinylpyrroles with phosphorus pentachloride. United States.
Rozinov, V G, Pensionerova, G A, Donskikh, V I, Sergienko, L M, Korostova, S E, Nikhaleva, A I, and Dolgushin, G V. 1986. "Phosphorus-containing enamines. IV. Reactions of alkyl- and phenyl-substituted 1-vinylpyrroles with phosphorus pentachloride". United States.
@article{osti_5416697,
title = {Phosphorus-containing enamines. IV. Reactions of alkyl- and phenyl-substituted 1-vinylpyrroles with phosphorus pentachloride},
author = {Rozinov, V G and Pensionerova, G A and Donskikh, V I and Sergienko, L M and Korostova, S E and Nikhaleva, A I and Dolgushin, G V},
abstractNote = {1-Vinylpyrroles, alkyl- and phenyl-substituted in the ring, are phosphorylated by phosphorus pentachloride in the ..cap alpha.. position of the pyrrole ring with the subsequent addition of the chlorophosphorane at the N-vinyl group with the formation of pyrrolo(1,2-a)-1,1,3-trichloro-4,1-azaphospholanium hexachlorophosphates. By treating the phosphorylation products with sulfur dioxide and triethylamine the authors synthesized pyrrolo(1,2-a)-1-oxo-1-chloro-4,1-azaphosphol-2-enes. The introduction of phenyl substituents into the nucleus of 1-vinylpyrroles or of alkyl substituents in the C/sup 2/ and C/sup 5/ positions is conducive to substitutive phosphorylation in the vinyl group and the formation of phosphorus-containing enamines. 1-Vinylindole and 9-vinylcarbazole are phosphorylated exclusively at the vinyl group. Hydrogen 1, phosphorus 32, and carbon 13 NMR spectra are analyzed in detail.},
doi = {},
url = {https://www.osti.gov/biblio/5416697}, journal = {J. Gen. Chem. USSR (Engl. Transl.); (United States)},
number = ,
volume = 56:4,
place = {United States},
year = {Sat Sep 20 00:00:00 EDT 1986},
month = {Sat Sep 20 00:00:00 EDT 1986}
}