Synthesis of 1,4-cyclohexadiene-based acetylenic macrocycles with Cadiot−Chodkiewicz coupling. structure of a tub-shaped tetrameric container

Bandyopadhyay, Arkasish ; Varghese, Babu ; Sankararaman, Sethuraman (2006) Synthesis of 1,4-cyclohexadiene-based acetylenic macrocycles with Cadiot−Chodkiewicz coupling. structure of a tub-shaped tetrameric container Journal of Organic Chemistry, 71 (12). pp. 4544-4548. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0605290

Related URL: http://dx.doi.org/10.1021/jo0605290

Abstract

The Cadiot−Chodkiewicz coupling of cis-1,4-diethynyl-1,4-dimethoxycyclohexa-2,5-diene and the corresponding ethynyl bromide gave a mixture of acetyenic macrocycles ranging from dimer to octamer in good isolable yields. The trimeric and tetrameric macrocycles have been structurally characterized by single-crystal X-ray crystallography. In the crystal structure of the trimeric macrocycle a molecule of benzene is sandwiched between a pair of macrocyles. The tetrameric macrocycle exhibited a tub-shaped conformation and encapsulated a molecule of ethyl acetate inside the tub.

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ID Code:109597
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