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Stereoselectivities in AgBF4-catalyzed and photoinduced phenyl-rearrangement of 2-chloropropiophenone

✍ Scribed by Satoshi Usui; Takeshi Matsumoto; Katsutoshi Ohkubo

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 240 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02284-9

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✦ Synopsis

S)-2-Phenylpropionic acid was stereoselectively obtained by the AgBF 4catalyzed phenyl-rearrangement of (S)-2-chloropropiophenone dimethyl acetal, while the photoirradiafion of (S)-or (R)-2-chloropropiophenone afforded partially racemized (S)or (R)-2-phenylpropionic acid, respectively. An intramolecular SN2 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.

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