Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
 
Chemistry of Anthracene–Acetylene Oligomers. XXIII. Molecular Structures and Stereochemistry of Anthracene–Diacetylene Cyclic Dimers Having Two Intraannular Alkoxy Groups
Shinji ToyotaTakuya TsuyaTetsuo Iwanaga
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Volume 86 (2013) Issue 11 Pages 1309-1316

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Abstract

Anthracene–diacetylene cyclic dimers having two alkoxy groups (OMe, OEt, or OPr groups) at the intraannular positions were synthesized by dimerization of 1,8-diethynylanthracene precursors. For the OEt and OPr compounds, anti- and syn-stereoisomers that differed in the direction of the alkyl groups were separated by chromatography. Kinetic measurements showed that the barriers to isomerization from syn-isomer to anti-isomer were 124 and >146 kJ mol−1 for the OEt and OPr compounds, respectively. The molecular structures of these compounds were examined by X-ray analysis and DFT calculations. The preference for anti-isomers is attributable to the intramolecular C–H···O hydrogen bonds. The effects of substituents on the molecular structures and the barriers to isomerization are discussed.

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© 2013 The Chemical Society of Japan
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