Reaction of 11, 11-dichlorotricyclo [4.4.1.01,6]-undeca-3, 8-diene (4) with potassium t-butoxide in dimethyl sulphoxide affords 1,6-methano[10]annulene (9) and 4-methylazulene (10); similar treatment of the dibromopropellane (5) yields the azulene (10), the mono-bromopropellane (11), but diminished yields of the annulene (9).
M. G. Banwell and C. Papamihail, J. Chem. Soc., Chem. Commun., 1981, 1182 DOI: 10.1039/C39810001182
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