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Marsh, Christopher Herbert (1962) Reactions of boron halides with amino-substituted anilines. Masters thesis, Northern Polytechnic.
As an extension of the work on amines and boron halides carried out at Northern Polytechnic, the addition products of the interaction of amino-substituted and phenyl-substituted anilines with boron trihalides and phenylboron dichloride were investigated.
2:1 Boron trihalide and phenylboron dichloride complexes were obtained with diamines; their structures were identified by infrared spectroscopy and their pyrolytic products were examined. Whereas the boron trichloride and boron tribromide complexes were shown to be of the type -X4BH3+NC6H4NHBX2, the boron trifluoride compounds were simple coordination complexes F3BH2NC6H4NH2BF3. Although the ditetrafluoroborates of diamines were isolated, no tetrabromoborates or tetrachloroborates could be prepared from the aryldiammonium dihalides and the corresponding boron trihalide which gave the 2:1 boron trihalide-diamine complex mentioned above.
The phenyl-substituted anilines gave 1:1 coordination complexes with boron trihalides and phenylboron dichloride, and not π complexes as were suggested for the 1:1 aniline-boron trihalide compounds.
Large scale preparations of 10-chloro-10:9-borasaro- phenanthrene, 2-phenyl-2,3-borazaindole and 2-phenyl-2,3- boroxindole were effected.
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