Enantiomeric resolution and absolute configuration of asymmetric derivatives of 3,7-dimethylenebicyclo(3. 3. 1)nonane. Synthesis of chiral derivatives of adamantane

Journal Article · Fri Jan 10 04:00:00 UTC 1986 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:6250500

Krasutskii, P A; Rodionov, V N; Chesskaya, N S; Yurchenko, A G

A new method was developed for the enantiomeric resolution of asymmetric derivatives of 3,7-dimethylenebicyclo(3.3.1)nonane by liquid chromatography on a chiral sorbent, i.e., silica gel impregnated with silver d-camphor-10-sulfonate. During transannular electrophilic cyclization and photocyclization the enantiomeric dienes, the absolute configurations of which were determined by means of the circular dichromism spectra, form chiral derivatives of adamantane with full retention of the optical purity.

• Research Organization: Kiev Polytechnic Institute, USSR
• OSTI ID: 6250500
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 21:8; ISSN JOCYA
• 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
ADAMANTANE
ADSORBENTS
ALKANES
ASYMMETRY
CAMPHOR
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHIRAL SYMMETRY
COMPLEXES
CYCLOALKANES
DEHYDROCYCLIZATION
DICHROISM
DIENES
ENANTIOMORPHS
EUROPIUM COMPLEXES
HYDROCARBONS
HYPERFINE STRUCTURE
ISOMERIZATION
KETONES
MAGNETIC CIRCULAR DICHROISM
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOTOCHEMICAL REACTIONS
POLYENES
RARE EARTH COMPLEXES
REAGENTS
SILICA GEL
SILVER COMPLEXES
SPECTRA
STEREOCHEMISTRY
SULFONATES
SYMMETRY
TERPENES
TRANSITION ELEMENT COMPLEXES
ULTRAVIOLET SPECTRA