Issue 0, 1973
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Wittig reactions of 1,2-dihydro-1,2-bis(triphenylphosphoranylidene) benzocyclobutene. Synthesis of all-cis- and mono-trans-1,2,3,4,6,7,8,9-octahydrodibenzo[b,h]benzo[3,4]cyclobuta[1,2-e]thionin, analogues of biphenylene containing a thionin ring

Peter J. Garratt,   Andrew B. Holmes,   Franz Sondheimer  and  K. Peter C. Vollhardt  

Abstract

A Wittig reaction between 1,2-dihydro-1,2-bis(triphenylphosphoranylidene)benzocyclobutene (5) and 2,2′-thio-biscyclohex-1-enecarbaldehyde (4) gave both all-cis-(7) and mono-trans-(8) 1,2,3,4,6,7,8,9-octahydrodibenzo[b,h]benzo[3,4]cyclobuta[1,2-e]thionin. Oxidation of the thionins with hydrogen peroxide gave the corresponding sulphoxides. In the case of the mono-trans-thionin (8), two isomeric sulphoxides were isolated, which differ only in the relative orientation of the oxygen atom and the trans-double bond. The barrier to ring inversion in these compounds must, therefore, be relatively high.

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Article information

DOI
https://doi.org/10.1039/P19730002253
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1973, 2253-2256

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Wittig reactions of 1,2-dihydro-1,2-bis(triphenylphosphoranylidene) benzocyclobutene. Synthesis of all-cis- and mono-trans-1,2,3,4,6,7,8,9-octahydrodibenzo[b,h]benzo[3,4]cyclobuta[1,2-e]thionin, analogues of biphenylene containing a thionin ring

P. J. Garratt, A. B. Holmes, F. Sondheimer and K. P. C. Vollhardt, J. Chem. Soc., Perkin Trans. 1, 1973, 2253 DOI: 10.1039/P19730002253

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