Annelation of 11,11-dichloro- and 11,11- dibromo-tricyclo[4.4.1.01,6] undeca-3,8-diene (6) with tetrachlorothiophen 1,1-dioxide is followed by an intramolecular Diels–Alder reaction to produce the hexacyclo [7.4.1.1.6,110.2,70.5,130.9,11] pentadec-3-ene system (9) which has the iceane skeleton contained within it.
D. P. G. Hamon and P. R. Spurr, J. Chem. Soc., Chem. Commun., 1982, 372 DOI: 10.1039/C39820000372
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