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

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

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

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Abstract

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.

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

Publication Date:: Fri Jan 10 00:00:00 EST 1986

Research Org.:: Kiev Polytechnic Institute, USSR

OSTI Identifier:: 6250500

Resource Type:: Journal Article

Journal Name:: J. Org. Chem. USSR (Engl. Transl.); (United States)

Additional Journal Information:: Journal Volume: 21:8; Other Information: Translated from Zh. Org. Khim.; 21: No.8, 1684-1691(Aug 1985)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 74 ATOMIC AND MOLECULAR PHYSICS; CYCLOALKANES; NMR SPECTRA; ENANTIOMORPHS; SILVER COMPLEXES; CATALYTIC EFFECTS; SULFONATES; ADAMANTANE; ASYMMETRY; CAMPHOR; CHIRAL SYMMETRY; DEHYDROCYCLIZATION; DIENES; EUROPIUM COMPLEXES; HYPERFINE STRUCTURE; ISOMERIZATION; MAGNETIC CIRCULAR DICHROISM; PHOTOCHEMICAL REACTIONS; REAGENTS; SILICA GEL; STEREOCHEMISTRY; ULTRAVIOLET SPECTRA; ADSORBENTS; ALKANES; CHEMICAL REACTIONS; COMPLEXES; DICHROISM; HYDROCARBONS; KETONES; ORGANIC COMPOUNDS; ORGANIC SULFUR COMPOUNDS; POLYENES; RARE EARTH COMPLEXES; SPECTRA; SYMMETRY; TERPENES; TRANSITION ELEMENT COMPLEXES; 400201* - Chemical & Physicochemical Properties; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory

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                    Krasutskii, P A, Rodionov, V N, Chesskaya, N S, and Yurchenko, A G. Enantiomeric resolution and absolute configuration of asymmetric derivatives of 3,7-dimethylenebicyclo(3. 3. 1)nonane. Synthesis of chiral derivatives of adamantane.  United States: N. p., 1986. 
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                    Krasutskii, P A, Rodionov, V N, Chesskaya, N S, & Yurchenko, A G. Enantiomeric resolution and absolute configuration of asymmetric derivatives of 3,7-dimethylenebicyclo(3. 3. 1)nonane. Synthesis of chiral derivatives of adamantane.  United States.

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                    Krasutskii, P A, Rodionov, V N, Chesskaya, N S, and Yurchenko, A G. 1986.  
        "Enantiomeric resolution and absolute configuration of asymmetric derivatives of 3,7-dimethylenebicyclo(3. 3. 1)nonane. Synthesis of chiral derivatives of adamantane".  United States.

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@article{osti_6250500,

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

  author       = {Krasutskii, P A and Rodionov, V N and Chesskaya, N S and Yurchenko, A G},

  abstractNote = {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.},

  doi          = {},

  url          = {https://www.osti.gov/biblio/6250500},
  journal      = {J. Org. Chem. USSR (Engl. Transl.); (United States)},
number       = ,

  volume       = 21:8,

  place        = {United States},

  year         = {Fri Jan 10 00:00:00 EST 1986},

  month        = {Fri Jan 10 00:00:00 EST 1986}

}

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