Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes

Ian W. Jones; Matthew A. Lynn; Eugene A. Mash

doi:10.1016/j.tet.2009.10.022

Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes

Ian W. Jones, Matthew A. Lynn, Eugene A. Mash

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Conformational analyses of bicyclo[m.m.m]alkanes where m=1-10 and of bicyclo[8.8.n]alkanes where n=1-7 bearing methyl groups on the bridgeheads were carried out using a Monte Carlo search strategy. In the bicyclo[m.m.m]alkane series, greater variability was observed for the inter-bridgehead distance for larger values of m. This suggests that properly substituted bicyclo[8.8.8]hexacosanes or larger ring systems might serve as molecular springs.

Original language	English (US)
Pages (from-to)	10317-10322
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2009.10.022
State	Published - Dec 12 2009

Keywords

Bicyclo[8.8.n]alkanes
Bicyclo[m.m.m]alkanes
Conformational analysis
Conformational compressibility
in,out-Stereoisomerism

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.10.022

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title = "Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes",

abstract = "Conformational analyses of bicyclo[m.m.m]alkanes where m=1-10 and of bicyclo[8.8.n]alkanes where n=1-7 bearing methyl groups on the bridgeheads were carried out using a Monte Carlo search strategy. In the bicyclo[m.m.m]alkane series, greater variability was observed for the inter-bridgehead distance for larger values of m. This suggests that properly substituted bicyclo[8.8.8]hexacosanes or larger ring systems might serve as molecular springs.",

keywords = "Bicyclo[8.8.n]alkanes, Bicyclo[m.m.m]alkanes, Conformational analysis, Conformational compressibility, in,out-Stereoisomerism",

author = "Jones, {Ian W.} and Lynn, {Matthew A.} and Mash, {Eugene A.}",

note = "Funding Information: We thank Dr. Dennis L. Lichtenberger for assistance. This work was supported by the University of Arizona Office of the Vice President for Research and by the Donors of the Petroleum Research Fund, administered by the American Chemical Society.",

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AU - Jones, Ian W.

AU - Lynn, Matthew A.

AU - Mash, Eugene A.

N1 - Funding Information: We thank Dr. Dennis L. Lichtenberger for assistance. This work was supported by the University of Arizona Office of the Vice President for Research and by the Donors of the Petroleum Research Fund, administered by the American Chemical Society.

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N2 - Conformational analyses of bicyclo[m.m.m]alkanes where m=1-10 and of bicyclo[8.8.n]alkanes where n=1-7 bearing methyl groups on the bridgeheads were carried out using a Monte Carlo search strategy. In the bicyclo[m.m.m]alkane series, greater variability was observed for the inter-bridgehead distance for larger values of m. This suggests that properly substituted bicyclo[8.8.8]hexacosanes or larger ring systems might serve as molecular springs.

AB - Conformational analyses of bicyclo[m.m.m]alkanes where m=1-10 and of bicyclo[8.8.n]alkanes where n=1-7 bearing methyl groups on the bridgeheads were carried out using a Monte Carlo search strategy. In the bicyclo[m.m.m]alkane series, greater variability was observed for the inter-bridgehead distance for larger values of m. This suggests that properly substituted bicyclo[8.8.8]hexacosanes or larger ring systems might serve as molecular springs.

KW - Bicyclo[8.8.n]alkanes

KW - Bicyclo[m.m.m]alkanes

KW - Conformational analysis

KW - Conformational compressibility

KW - in,out-Stereoisomerism

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Conformational analysis of bridgehead-substituted bicyclo[m.m.m]alkanes and bicyclo[8.8.n]alkanes

Abstract

Keywords

ASJC Scopus subject areas

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