Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.

Abstract: A process is disclosed which comprises: contacting a catalyst such as alumina silica, aluminosilicates, titanium oxide, magnesium oxide, and the metals of Groups III and IIB of the Periodic Table under reducing conditions with a gaseous mixture comprising elemental chlorine gas and a diluent under conditions effective to improve the ability of the catalyst to dehydrohalogenate halogenated hydrocarbons: contacting the catalyst with a halogenated hydrocarbon feedstock, the halogenated hydrocarbon feedstock with or without a carrier gas, in the gas phase under dehydrohalogenation conditions; and recovering a dehydrohalogenated product.