Circular Dichroism and Conformational Analysis of Diastereomeric Bicamphors

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Title:Circular Dichroism and Conformational Analysis of Diastereomeric Bicamphors
Creators:
Boiadjiev, Stefan E.
Lightner, David A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 4, pp. 477-489
Uncontrolled Keywords:Molecular mechanics, NMR spectroscopy, <sup>1</sup>H and <sup>13</sup>C, Camphor dimers, Stereochemistry, CD spectroscopy, Conformation analysis, Terpenoids, UV spectroscopy

Abstract

Stereospecific syntheses afforded <i>endo</i>,<i>endo-</i> (<strong>1</strong>) and <i>exo,exo-</i> (<strong>2</strong>) bicamphors, while the third possible diastereomeric <i>exo</i>,<i>endo-</i>bicamphor (<strong>3</strong>) originated from nonselective camphor radical dimerization. The stereochemistry of bicamphor linkage was confirmed by <sup>1</sup>H&nbsp;NMR analysis. Chiroptical and ultraviolet spectral data are presented for the three diastereomers <strong>1</strong>-<strong>3</strong> to show interchromophoric interaction. Conformational analysis to evaluate the relative orientation of each pair of carbonyl chromophores was accomplished by <sup>1</sup>H&nbsp;NMR spectroscopy and molecular mechanics calculations. <p>

Title:Circular Dichroism and Conformational Analysis of Diastereomeric Bicamphors
Creators:
Boiadjiev, Stefan E.
Lightner, David A.
Uncontrolled Keywords:Molecular mechanics, NMR spectroscopy, <sup>1</sup>H and <sup>13</sup>C, Camphor dimers, Stereochemistry, CD spectroscopy, Conformation analysis, Terpenoids, UV spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:4
Page Range:pp. 477-489
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000477UNSPECIFIED
ID Code:1655
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Boiadjiev, Stefan E.; Lightner, David A. (2000) Circular Dichroism and Conformational Analysis of Diastereomeric Bicamphors. Collection of Czechoslovak Chemical Communications, 65 (4). pp. 477-489. ISSN 0010-0765

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