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organic compounds
The reaction of sp-9-(o-tert-butylphenyl)-9-fluorenol, (1), with thionyl chloride in CHCl3 at room temperature quantitatively provided the title compound [(2), (C23H21Cl], instead of the expected 9-(o-tert-butylphenyl)-9-chlorofluorene. Chlorination of an alkyl group under the conditions in which (1) was converted into (2) is apparently unprecedented. While the unexpected structure of (2) was suggested by 1H and 13C NMR, unequivocal characterization required X-ray crystallographic analysis. Surprisingly, introduction of the Cl atom in (2) imposes only a few minor changes in the bonding parameters compared with its non-chlorinated counterpart, sp-9-(o-tert-butylphenyl)fluorene.