Collect. Czech. Chem. Commun. 1990, 55, 256-260

The thermal dealkylation of 2-chloro-4,6-bis(bornyl- and norbornylamino)-s-triazines

Živorad D. Tadić, Bratislav Ž. Jovanovic and Dušan G. Antonović

Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Yugoslavia


The thermal dealkylation of 2-chloro-4,6-bis(isobornylamino)-s-triazine (I), 2-chloro-4,6-bis(bornylamino)-s-triazine (II), 2-chloro-4,6-bis(exo-norbornylamino)-s-triazine (III) and 2-chloro-4,6-bis(endo-norbornylamino)-s-triazine (IV) was performed at 250 °C. The high degree of dealkylation in the case of isobornyl derivative I was ascribed to a reaction via a seven-membered cyclic transition state, as well as to steric interaction of the dimethylmethylene group and the triazine ring. The presence of tricyclenes in the dealkylation products of this derivative also indicates that the reaction partially takes place with charge separation, i.e. by the anchimeric assistance of the C-6 atom. The lower degree of dealkylation of bornyl derivative II is in agreement with the lower reactivity of the endo-isomer and probably takes place via three different transition states yielding three products. The dealkylation of norbornyl derivatives (exo-III and endo-IV) was successful only in the case of the exo-isomer yielding the expected products, while the endo-isomer under these experimental conditions did not give any dealkylation products.