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Synthesis of Medium and Large Ring Compounds, XLIII. Synthesis and Isomerization of 8,9-Dimethyl[6]paracyclophane and Its Bridged Dewar Isomer

✍ Scribed by Tochtermann, Werner ;Rodefeld, Lars ;Dreeskamp, Herbert ;Sarge, Stefan M.

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
280 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

An improved sonochemical procedure for the synthesis of dimethyl [6]paracyclophane‐8,9‐dicarboxylate (2a) on a 10‐g scale is described. The title compound 2d was synthesized from 2a in three steps. Irradiation of 2d yielded the Dewar isomer 3. In solution, the reaction enthalpy for the thermal isomerization of 3 to 2d was determined to be ‐162 ± 16 kJ · mol^‐1^, while the activation energy for this reaction was found to be 123 ± 12 kJ · mol^‐1^.

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