Abstract

2,4,6-Triisopropylstryrene was synthesized in a single step via the Witting
Reaction from the corresponding aldehyde. The reaction of three styrene's
derivatives, 2,6-dimethylstyrene, 2,4,6-trimethylstyrene, and 2,4,6-
triisopropylstyrene with 4-methyl-l,2,4-triazoline-3,5-dion(M eTD) was
investigated. These reactions are instantaneous at room temperature and lead to the
formation of 2: 1 adducts in high yield via double Diels-Alder reactions. In each case
the initially formed 1:l Diels-Alder adduct is extremely reactive, and was not
isolated. It readily undergoes the second Diels- Alder reaction with MeTD. These
2:l adducts wete fully characterized by IR, CNMR(o ff- resonace, INEPT,
multiplicity determination sequence techniques), mass spectra, 'HNMR and
elemental analysis.