S. Usui, Takeshi Matsumoto, K. Ohkubo
Dec 24, 1998
Citations
0
Influential Citations
4
Citations
Journal
Tetrahedron Letters
Abstract
Abstract ( S )-2-Phenylpropionic acid was stereoselectively obtained by the AgBF 4 -catalyzed phenyl-rearrangement of ( S )-2-chloropropiophenone dimethyl acetal, while the photoirradiation of ( S )- or ( R )-2-chloropropiophenone afforded partially racemized ( S )- or ( R )-2-phenylpropionic acid, respectively. An intramolecular S N 2 mechanism is suggested for the former rearrangement. The latter result is indicative of the intervention of an ion or radical intermediate in the photoinduced phenyl-rearrangement.