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

Journal Article · Sat Sep 20 04:00:00 EDT 1986 · J. Gen. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5416697

Rozinov, V G; Pensionerova, G A; Donskikh, V I; Sergienko, L M; Korostova, S E; Nikhaleva, A I; Dolgushin, G V

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.

• Research Organization: A. A. Zhdanov Irkut-sk State Univ. (USSR)
• OSTI ID: 5416697
• Journal Information: J. Gen. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Gen. Chem. USSR (Engl. Transl.); (United States) Vol. 56:4; ISSN JGCHA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
640302 -- Atomic
Molecular & Chemical Physics-- Atomic & Molecular Properties & Theory
74 ATOMIC AND MOLECULAR PHYSICS
AMINES
AROMATICS
AZAARENES
AZOLES
CARBAZOLES
CARBON 13
CARBON ISOTOPES
CHALCOGENIDES
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATION
CHLORINE COMPOUNDS
CHLOROFORM
COUPLING
COUPLING CONSTANTS
ELECTRON DENSITY
ELECTRONIC STRUCTURE
EVEN-ODD NUCLEI
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HETEROCYCLIC COMPOUNDS
HYDROGEN 1
HYDROGEN ISOTOPES
HYPERFINE STRUCTURE
INDOLES
INFRARED SPECTRA
INTERMEDIATE COUPLING
ISOTOPES
J-J COUPLING
LIGHT NUCLEI
MOLECULAR STRUCTURE
MULTIPLETS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PHOSPHORUS 31
PHOSPHORUS CHLORIDES
PHOSPHORUS COMPOUNDS
PHOSPHORUS ISOTOPES
PHOSPHORYLATION
PYRROLES
SPECTRA
STABLE ISOTOPES
SULFUR COMPOUNDS
SULFUR DIOXIDE
SULFUR OXIDES
SYNTHESIS