Tetrahedron Letters p. 1417 - 1420 (1996)
Update date:2022-08-16
Topics:
Jenner, Gerard
Papadopoulos, Mihail
The AlCl3 catalyzed addition of methyl propynoate to cyclopentene and cyclohexene is examined by high pressure kinetics. The reaction affords either a [2+2] cycloadduct (with cyclopentene) with an activation volume ΔV≠ of -20 cm3.mol-1 or in the case of cyclohexene, an ene adduct together with the [2+2] product. The chemoselectivity of the cyclohexene reaction is not affected by pressure indicating an equal ΔV≠ - value for the ene and [2+2] reactions. These results suggest a dipolar acyclic transition state with a common intermediate for the catalyzed ene and [2+2] addition reactions.
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