Solvent-dependent changes in the ene reaction of RTAD with alkenes: the cyclopropyl group as a mechanistic probe.
[reaction: see text] The vinylcyclopropyl moiety was used as an efficient probe to test mechanistic possibilities of the triazolinedione-alkene ene reaction. In non-hydroxylic solvents, this reaction afforded only the ene adducts via a closed three-membered aziridinium imide (AI) intermediate, whereas in hydroxylic solvents a dipolar intermediate is favored and trapped by the cyclopropyl moiety to form the corresponding cyclopropyl-rearranged solvent-trapped adducts.
Roubelakis
Manolis M
MM
Department of Chemistry, University of Crete, Greece.
Vougioukalakis
Georgios C
GC
Angelis
Yiannis S
YS
Orfanopoulos
Michael
M