Thermal dealkylation of 2,4-bis(alkylamino)-6-chloro-s-triazines. Effect of alkyl group structure. Part 2

Abstract

Two series of NN′-dialkyl derivatives of 2,4-diamino-6-chloro-s-triazines (alkyl groups RCH₂CHMe and RCH₂CMe₂ where R = Me, Et, Prⁱ, or Bu^t) were thermally dealkylated, and the mixtures of olefinic products were analysed by g.l.c. In the series of secondary alkyl derivatives, alkyl group branching caused an increase in the trans- to cis-2-olefin ratio, while the 1-ene to 2-ene ratio remained practically unchanged. In the series of tertiary alkyl derivatives there was an increase in the 1-ene to 2-ene ratio. Both facts are interpreted in terms of increased non-bonding interactions of the alkyl groups on the α- and β-carbon atoms in the transition state.