Tetrahedron p. 8547 - 8554 (1999)
Update date:2022-08-24
Topics:
De La Torre, Maria Fe
Caballero, M. Cruz
Whiting, Andrew
Comparative studies were carded out on boron trifluoride etherate, phenylboron difluoride and meta-nitrophenylboron difluoride for the Lewis acid catalysed Diels-Alder reaction of cyclopentadiene and a range of standard dienophiles in tetrahydrofuran solution. Phenylboron difluoride showed remarkably similar reactivity in terms of yield and endo to exo selectivity to boron trifluoride, whereas meta-nitrophenylboron difluoride was more reactive than either boron trifluoride or phenylboron difluoride and showed more marked differences in endo: exo ratios. These results contrast to some extent with gas-phase semi-empirical calculations (PM3), which suggest that boron trifluoride and meta-nitrophenylboron difluoride should have similar reactivity; phenylboron difluoride being less reactive. However, since arylboron difluorides are easily prepared, these Lewis acids represent a group of potentially highly tuneable catalysts for Diels-Alder reactions.
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Doi:10.1016/S0022-1139(00)82671-8
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