Reactions of adducts of dichloro(phenyl)borane with aromatic amines in boiling benzene

Abstract

A comparison is made of the elimination of hydrogen chloride from certain adducts of arylamines with dichloro(phenyl)borane and the corresponding arylammonium trichloro(phenyl)borates, with previous data on related boron trichloride adducts.¹ Between 1 and 2 of the theoretical number of mol of hydrogen chloride are evolved from dichloro(phenyl)borane systems, exactly 2 mol from the trichloro(phenyl)borates and usually >1 mole from the boron trichloride adducts. The products of these reactions are complex but no borazoles were obtained. The dimethylaniline adduct of dichloro(phenyl)borane evolved no gaseous hydrogen chloride, and substitution of boron in the arylamine ring is implied.