Racemisation and rearrangement of 1,2-dihydro-1,3,5-triazines: a novel reversible thermal electrocyclic reactionElectronic supplementary information (ESI) available: Arrhenius plot for racemisation of enantiomers of 1d. See http://www.rsc.org/suppdata/cc/b1/b101245m/

Abstract

Chiral 1,2-diaryl-1,2-dihydro-4,6-diamino-1,3,5-triazines undergo facile racemisation by a reversible thermal electrocyclic reaction mechanism; the transient intermediate can lead, after tautomerisation, to rearranged racemic 2-aryl-1,2-dihydro-4-amino-6-anilino-1,3,5-triazines.