New reagent systems for electrophilic chlorination of aromatic compounds: organic chlorine-containing compounds in the presence of silica

In the presence of silica, a number of chlorine-containing organic compounds, such as N,N-dichlorourethane, dichloramine-T, and t-butyl hypochlorite, become active electrophilic reagents capable of controlled monochlorination of aromatic compounds under mild conditions; for example, t-butyl hypochlorite/silica chlorinates alkylbenzenes, naphthalene, and anisole readily at 25°C; N,N-dichlorourethane/silica chlorinates benzene within 2 days 50°C