Author :
Mallakpour, S. E.,Butler, G. B
Title of Article :
Reaction of 4-methyl-1,2,4-triazoline-3,5-dione with di and tri-substituted styrenes
Descriptors :
1,2,4-triazoline- 3,5- dione,Rearrangement
Abstract :
2,4,6-Triisopropylstryrene was synthesized in a single step via Witting Reaction from the corresponding aldehyde. The reaction of three styreneʹs derivatives, 2,6-dimethylstyrene, 2,4,6-trimethlstyrene, and 2,4,6-triisopropylstyrene with 4-methyl-1,2,4-triazoline-3,5-dione (MeTD) was investigated. These reactions are instantaneous at room temperature and lead to the formation of 2:1 adducts in high vield via double Diels-Alder reactions.In each case the initially formed 1:1 Diels-Alder adduct is extremely reactive, and was not isolated. It readily undergoes the second Diels- Alder reaction with MeTD. These 2:1 adducts were fully characterized by IR, CNMR (off - resonace, INEPT, multiplicity determination sequence techniques), mass spectra, HNMR and elemental analysis.
