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Stereochemistry of seven-membered heterocycles. communication 16. dipole moments, IR, /sup 1/H, and /sup 13/C nmr spectra, and conformations of 4-methyl-, 4-phenyl-, and isomeric 4,7-dimethyl-2,2-pentamethylene-1,3-dioxa-5,6-benzocycloheptenes

Journal Article · · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
DOI:https://doi.org/10.1007/BF00956083· OSTI ID:5035778
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In order to study the effect of the substituents at the benzyl carbon atoms on the conformational composition, the authors investigated the dynamic /sup 1/H and /sup 13/C NMR spectra of groups II-IV, the IR spectra of II, IV, and V and the dipole moments of IV and V. The measurements showed that the conformational mobility of 4-methyl-, 4-phenyl-, and trans-4,7-dimethyl-2,2-pentamethylene-1,3-dioxa-5,6-benzocycloheptenes is a consequence of the cyclohexane ring with rigid twist conformation of the heterocycle. The NMR signals of the benzyl protons of the heterocycle were assigned. The corresponding cis isomer exists as a conformational mixture of chair and twist forms.

Research Organization:
A.M. Butlerov Chemical Institute, Lenin Kazan State Univ.
OSTI ID:
5035778
Journal Information:
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 34:6, PT. 1; ISSN BACCA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKENES
CARBON 13
CARBON ISOTOPES
CONFORMATIONAL CHANGES
DIPOLE MOMENTS
EVEN-ODD NUCLEI
HEPTENES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROGEN 1
HYDROGEN ISOTOPES
INFRARED SPECTRA
ISOMERS
ISOTOPES
LIGHT NUCLEI
MAGNETIC DIPOLE MOMENTS
MAGNETIC MOMENTS
NMR SPECTRA
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
SPECTRA
STABLE ISOTOPES
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS