SELECTIVE FUNCTIONALISATION-7; CHLORINATION OF AROMATIC COMPOUNDS IN THE PRESENCE OF TENTACLE MOLECULES WITH PYRIDINIUM HEAD GROUPS

Article abstract of DOI:10.1016/S0040-4020(01)91108-1

tris-Pyridiniumalkyl triesters of benzene-1,3,5-tricarboxylic acid 3,6 and 11 carbon atoms in the alkyl chain interact with aromatic substrates, phenol, anisole, diphenyl ether and naphthalene in a manner dependent upon the struture of the substrate.Thus all three tentacle molecules interact with phenol through the pyridinium head group as shown by (1)H NMR (250 MHz) and confirmed by inhibition of chlorination of the bound phenol.The remaining substrates interact but away from the head group; chlorination is also inhibited.In these cases, a contributor to the low reactivity of the substrates to chlorination in the presence of the tentacle molecules is shown to be the unexpected inactivation of the chlorinating agent, t-butyl hypochlorite, by the tentacle molecules.