ChemInform Abstract: Hydrodehalogenation of Halogenated Aryl Ketones under Multiphase Conditions. Part 6. pH Effect on the Chemoselectivity and Preliminary Mechanistic Investigation.

✍ Scribed by Alvise Perosa; Maurizio Selva; Pietro Tundo

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199937049

✦ Synopsis

Hydrodehalogenation of Halogenated Aryl Ketones under Multiphase Conditions. Part 6. pH Effect on the Chemoselectivity and Preliminary Mechanistic Investigation.

-Chloropropiophenone (I) is used as model compound to study hydrodehalogenation reactions under multiphase conditions at varying pH. The chemoselectivity of this reaction strictly depends on the KOH concentration of the aqueous phase leading either to alcohol (II) (at higher KOH concentrations) or ketone (IV) (at low KOH concentrations). In acidic aqueous phase, chemoselectivity is directed towards aromatic ring reduction products (V) and (VI). The reaction mechanism is discussed. Further investigations are underway to take advantage of these features for synthetic applications. -(PEROSA, ALVISE; SELVA, MAURIZIO; TUNDO, PIETRO;