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Hydrogen Transfer Reactions, 6. Dehydrogenation of 1,2-Dihydroarenes by Quinones: Regio- and Stereoselectivity in the Two-Step Mechanism
Paukstat, Ralf,Brock, Martin,Heesing, Albert
, p. 2579 - 2592 (2007/10/02)
1,2-Dihydronaphthalene (1) is dehydrogenated by o- and p-quinones in a two-step mechanism.In the rate determining step a hydride ion is abstracted from the 2-position by o-chloro- (4a) and o-bromoanil (4b) with high regioselectivity.Ion pairing leads to highly stereoselective cis-elimination of the proton.Stereoselectivity, primary isotope effects, and activation entropy are consistent with a coplanar coordination in the transition state and participation of tunneling. p-Quinones show different regioselectivity in the hydride abstraction step.The dehydrogenation of 9,10-dihydrophenanthrene (3) proceeds in a similar way.
