Issue 2, 1990

Synthesis and properties of methanothia-[15]-, -[17]-, -[19]-, -[21]-, -[23]-, -[25]-, -[27]-, -[29]-annulene and dimethanodithia-[26]- and -[30]-annulene

Abstract

Double Wittig reactions of the vinylogues of cyclohepta-1,3,5-triene-1,6-dicarbaldehyde with bis[(triphenylphosphonio)methyl] sulphide dibromide afforded the corresponding monomeric and/or dimeric condensation products, i.e. singly methano-bridged thia-annulenes and/or doubly methano-bridged dithia-annulenes; their 1H NMR spectra showed that the methanothia-[17]-, -[19]-, -[23]-, and -[27]-annulene sustain ring current, while the methanothia-[15]-, -[21]-, -[25]-, and -[29]-annulene as well as the dimethanodithia-[26]- and -[30]-annulene do not. Dynamic NMR analysis of the methylene protons revealed the flipping of the methylene bridge above and below the average plane of the macrocycle.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 333-343

Synthesis and properties of methanothia-[15]-, -[17]-, -[19]-, -[21]-, -[23]-, -[25]-, -[27]-, -[29]-annulene and dimethanodithia-[26]- and -[30]-annulene

J. Ojima, T. Hashimoto, J. Katsuyama, H. Miyashita, S. Fujita, S. Kuroda, Y. Kano and G. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 1990, 333 DOI: 10.1039/P19900000333

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