One-azabicyclic compounds. 22. Stereochemistry and /sup 13/C NMR spectra of salts of pyrrolizidine and its homologs with protonic acids

Journal Article · Sun Jun 01 04:00:00 EDT 1986 · Chem. Heterocycl. Compd. (Engl. Transl.); (United States)

OSTI ID:6335262

Subbotin, O A; Skvortsov, I M

/sup 13/C NMR spectra were obtained for pyrrolizidinium salts and their homologs and their signals were assigned. With the exception of highly strained cis-3,8-H-cis-5,8-H-3,5-dimethylpyrrolizidine (VI), all the bases studied upon their direct mixing with CF/sub 3/CO/sub 2/H form salts only with cis-fused rings in the cation. Mixtures of salts with cis- and trans-fused pyrrolizidinium fragments are formed upon the reaction of cis-3,8-H-methyl- (III) and cis-3,8-H-cis-5,8-H-3,5-dimethylpyrrolizidine (VI) under conditions close to those for kinetically-controlled amine protonation. The /sup 13/C NMR spectra of the isomeric pyrrolizidinium salts obtained as a result of the absorption of base VI by sulfuric acid were used to evaluate the conformational equilibrium in the starting compound VI. The /sup 13/C NMR chemical shifts of unsubstituted trans-fused pyrrolizidinium salts were predicted.

• Research Organization: M.V. Lomonosov Moscow State Univ., USSR
• OSTI ID: 6335262
• Journal Information: Chem. Heterocycl. Compd. (Engl. Transl.); (United States), Journal Name: Chem. Heterocycl. Compd. (Engl. Transl.); (United States) Vol. 21:12; ISSN CHCCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ABSORPTION
ACETATES
ACETIC ACID
ACETONITRILE
ACIDIFICATION
AMINES
AMMONIUM COMPOUNDS
AZOLES
BARYONS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID SALTS
CARBOXYLIC ACIDS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CONFORMATIONAL CHANGES
DEUTERIUM COMPOUNDS
ELEMENTARY PARTICLES
EVEN-ODD NUCLEI
FERMIONS
HADRONS
HETEROCYCLIC COMPOUNDS
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYDROGEN TRANSFER
INORGANIC ACIDS
ISOMERIZATION
ISOTOPES
ISOTOPIC EXCHANGE
LIGHT NUCLEI
MONOCARBOXYLIC ACIDS
NITRILES
NMR SPECTRA
NUCLEI
NUCLEONS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXYGEN COMPOUNDS
PROTONS
PYRROLES
PYRROLIDINES
QUATERNARY COMPOUNDS
SALTS
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SULFATES
SULFUR COMPOUNDS
SULFURIC ACID