Abstract
Palladations of the diastereomeric 4-(4- tert-butyl-2-oxazolinyl)-[2.2]paracyclophanes ( S, R p )- 3 and ( S, S p )- 3 have been investigated. Exclusive ortho-palladation occurs, when ( S, R p )- 3 is treated with Pd(OAc) 2 in glacial acetic acid. In contrast, ( S, S p )- 3 affords products from either metallation in the ortho or the benzylic position of the [2.2]paracyclophane skeleton depending on the reaction conditions. Upon treatment of the resulting complexes with LiCl followed by addition of PPh 3 mononuclear chloro{4-(2-oxazolinyl)-[2.2]paracyclophane,5- C,3- N}(triphenylphosphine)palladium(II) complexes ( S, S p )- 7, ( S, R p )- 7, and ( S, S p )- 9 have been obtained. The solid state structures of ( S, S p )- 7 and ( S, R p )- 7 have been determined by X-ray diffraction analysis. Reaction of ortho-palladated complexes ( S, S p )- 7 and ( S, R p )- 7 with KPPh 2 gives the corresponding planar-chiral phosphines ( S, S p )- 11 and ( S, R p )- 11, respectively. From benzyl substituted complex ( S, S p )- 9 bromo derivative ( S, S p )- 12 was obtained.
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