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Stereochemical dependence of isotope effects in the ene reaction of N-phenyl-1,2,4-triazoline-3,5-dione with isomers of butene-d3

1987; Elsevier BV; Volume: 28; Issue: 1 Linguagem: Inglês

10.1016/s0040-4039(00)95637-5

1873-3581

Michael Orfanopoulos, Christopher S. Foote, Ioulia Smonou,

Fluorine in Organic Chemistry

The magnitude of the primary isotope effect of the title reaction depends on the relative stereochemistry of the competing groups, being large when the groups are cis and small when they are on opposite sides of the double bond. An intermediate such as a diaziridinium imide is required to rationalize the results.