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Reactions of triazolinedione with alkenes. A remarkable geminal selectivity.

1990; Elsevier BV; Volume: 31; Issue: 40 Linguagem: Inglês

10.1016/s0040-4039(00)97956-5

1873-3581

Michael Orfanopoulos, Yiannis Elemes, Manolis Stratakis,

Chemical Reaction Mechanisms

Abstract The ene reaction of N-Phenyl-1,2,4-triazoline-3,5-dione with alkenes shows a remarkable preference for hydrogen abstraction from the group which is geminal to the larger substituent of the double bond. These results require that the dominant effect in the transition state of the ene reaction is the nonbonded interactions.