The photochemical addition of 2,2,2-trifluoroethanol to methoxy-substituted stilbenes.
The excited-state lifetime of the trans-stilbene chromophore in acetonitrile is prolonged by methoxy substituents in the meta positions. The long-lived singlet excited state of trans-3,5-dimethoxystilbene (trans-2d) is quenched upon the addition of 2,2,2-trifluoroethanol (TFE), and the Markovnikov ether is observed as the major product from steady-state irradiations. The results indicate that the reaction pathway proceeds through a carbocation intermediate.
Roberts
Jeffrey C
JC
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3.
Pincock
James A
JA