Hickinbottom

Fluorophenyl isocyanate [1195-45-5] M 137.1, b 55°/8mm, n 1.514. Purify by repeated fractionation through an efficient column. If IR indicated that there is too much urea (in the presence of moisture the symmetrical urea is formed) then dissolve in dry EtOH-free CHCI3, filter, evaporate and distil. It is a pungent LACHRYMATORY liquid, [see Hardy J Chem Soc 2011 1934-, and Hickinbottom Reactions of Organic Compounds Longmans p. 493 1957.]... 

The first reaction probably involving attack by benzyl radicals on a heterocyclic system was reported by Hickinbottom. - He found that, when benzyl phenyl ether is heated in quinoline to about 250 C, benzylquinoline and hydroxyphenylquinolines are the main products. 

W. J. Hickinbottom, Reactions of Organic Compounds, Longmans-Green, London 1950. 

It is also possible to carry out the reaction by heating the amine (not the salt) at a temperature between 200 and 350°C with a metal halide such as C0CI2, CdCl2, or ZnCl2. When this is done, the reaction is called the Reilly-Hickinbottom rearrange-... 

Blackwell Hickinbottom J. Chem. Soc. 1961, 1405 Avendano de Diego Elguero Monatsh. Chem. 1999,121, 649. 

For example, Ayad Beard Garwood Hickinbottom J. Chem. Soc. 1957, 2981 Coulson Williams Johnston J. Chem. Soc. B 1967, 174. 

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