Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes

Richard S Glass, John R. Duchek, Usha Devi G Prabhu, William N. Setzer, George S. Wilson

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Abstract

The synthesis and structure elucidations of several 2-endo-substituted-6-endo-(methylthio)-, 2-exo-substituted-6-endo-(methylthio)-, 2-endo-substituted-6-exo-(methylthio)-, and 2-exo-substituted-6-exo-(methylthio)-bicyclo[2.2.1]heptanes, 2-5, respectively, are reported. The structure proofs involved a combination of spectroscopic, X-ray crystallographic, and equilibration studies. The crystal and molecular structures of 6-endo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (2a) and 6-exo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (4a) were determined by X-ray crystallographic techniques. These compounds crystallize in the space groups Pbca and P21/n, respectively, with a = 13.040 (2) Å, b = 10.877 (3) Å, c = 13.518 (3) Å, Z = 8, and a = 12.740 (2) Å, b = 6.200 (1) Å, c = 13.146 (2) Å, β = 114.81 (1)°, Z = 4, respectively. The nonhydrogen atoms were located in each case by direct methods. Full-matrix least-squares refinement led to conventional R factors of 0.0466 and 0.0389, respectively, after several cycles of anisotropic refinement. These molecular structure determinations revealed an unsymmetrical contra twist of the norbornyl skeleton in endo acid 2a and an unsymmetrical synchro twist in endo acid 4a.

Original languageEnglish (US)
Pages (from-to)3640-3646
Number of pages7
JournalJournal of Organic Chemistry
Volume45
Issue number18
StatePublished - 1980

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Carboxylic Acids
Molecular structure
X rays
Acids
R Factors
Crystal structure
Atoms
bicyclo(2.2.1)heptene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Glass, R. S., Duchek, J. R., Prabhu, U. D. G., Setzer, W. N., & Wilson, G. S. (1980). Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes. Journal of Organic Chemistry, 45(18), 3640-3646.

Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes. / Glass, Richard S; Duchek, John R.; Prabhu, Usha Devi G; Setzer, William N.; Wilson, George S.

In: Journal of Organic Chemistry, Vol. 45, No. 18, 1980, p. 3640-3646.

Research output: Contribution to journalArticle

Glass, RS, Duchek, JR, Prabhu, UDG, Setzer, WN & Wilson, GS 1980, 'Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes', Journal of Organic Chemistry, vol. 45, no. 18, pp. 3640-3646.
Glass, Richard S ; Duchek, John R. ; Prabhu, Usha Devi G ; Setzer, William N. ; Wilson, George S. / Synthesis and characterization of 2-substituted 6-(methylthio)bicyclo[2.2.1]heptanes. In: Journal of Organic Chemistry. 1980 ; Vol. 45, No. 18. pp. 3640-3646.
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abstract = "The synthesis and structure elucidations of several 2-endo-substituted-6-endo-(methylthio)-, 2-exo-substituted-6-endo-(methylthio)-, 2-endo-substituted-6-exo-(methylthio)-, and 2-exo-substituted-6-exo-(methylthio)-bicyclo[2.2.1]heptanes, 2-5, respectively, are reported. The structure proofs involved a combination of spectroscopic, X-ray crystallographic, and equilibration studies. The crystal and molecular structures of 6-endo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (2a) and 6-exo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (4a) were determined by X-ray crystallographic techniques. These compounds crystallize in the space groups Pbca and P21/n, respectively, with a = 13.040 (2) {\AA}, b = 10.877 (3) {\AA}, c = 13.518 (3) {\AA}, Z = 8, and a = 12.740 (2) {\AA}, b = 6.200 (1) {\AA}, c = 13.146 (2) {\AA}, β = 114.81 (1)°, Z = 4, respectively. The nonhydrogen atoms were located in each case by direct methods. Full-matrix least-squares refinement led to conventional R factors of 0.0466 and 0.0389, respectively, after several cycles of anisotropic refinement. These molecular structure determinations revealed an unsymmetrical contra twist of the norbornyl skeleton in endo acid 2a and an unsymmetrical synchro twist in endo acid 4a.",
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AU - Duchek, John R.

AU - Prabhu, Usha Devi G

AU - Setzer, William N.

AU - Wilson, George S.

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N2 - The synthesis and structure elucidations of several 2-endo-substituted-6-endo-(methylthio)-, 2-exo-substituted-6-endo-(methylthio)-, 2-endo-substituted-6-exo-(methylthio)-, and 2-exo-substituted-6-exo-(methylthio)-bicyclo[2.2.1]heptanes, 2-5, respectively, are reported. The structure proofs involved a combination of spectroscopic, X-ray crystallographic, and equilibration studies. The crystal and molecular structures of 6-endo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (2a) and 6-exo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (4a) were determined by X-ray crystallographic techniques. These compounds crystallize in the space groups Pbca and P21/n, respectively, with a = 13.040 (2) Å, b = 10.877 (3) Å, c = 13.518 (3) Å, Z = 8, and a = 12.740 (2) Å, b = 6.200 (1) Å, c = 13.146 (2) Å, β = 114.81 (1)°, Z = 4, respectively. The nonhydrogen atoms were located in each case by direct methods. Full-matrix least-squares refinement led to conventional R factors of 0.0466 and 0.0389, respectively, after several cycles of anisotropic refinement. These molecular structure determinations revealed an unsymmetrical contra twist of the norbornyl skeleton in endo acid 2a and an unsymmetrical synchro twist in endo acid 4a.

AB - The synthesis and structure elucidations of several 2-endo-substituted-6-endo-(methylthio)-, 2-exo-substituted-6-endo-(methylthio)-, 2-endo-substituted-6-exo-(methylthio)-, and 2-exo-substituted-6-exo-(methylthio)-bicyclo[2.2.1]heptanes, 2-5, respectively, are reported. The structure proofs involved a combination of spectroscopic, X-ray crystallographic, and equilibration studies. The crystal and molecular structures of 6-endo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (2a) and 6-exo-(methylthio)bicyclo[2.2.1]heptane-2-endo-carboxylic acid (4a) were determined by X-ray crystallographic techniques. These compounds crystallize in the space groups Pbca and P21/n, respectively, with a = 13.040 (2) Å, b = 10.877 (3) Å, c = 13.518 (3) Å, Z = 8, and a = 12.740 (2) Å, b = 6.200 (1) Å, c = 13.146 (2) Å, β = 114.81 (1)°, Z = 4, respectively. The nonhydrogen atoms were located in each case by direct methods. Full-matrix least-squares refinement led to conventional R factors of 0.0466 and 0.0389, respectively, after several cycles of anisotropic refinement. These molecular structure determinations revealed an unsymmetrical contra twist of the norbornyl skeleton in endo acid 2a and an unsymmetrical synchro twist in endo acid 4a.

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