Photochemical loss of a chloride anion from an α-chloroketone. The photolysis of exo-3-chlorobicyclo[2.2.1]hept-5-en-2-one in methanol.

✍ Scribed by Bruce Emil Kaplan; August Lenn Hartwig

• Book ID: 104222556
• Publisher: Elsevier Science
• Year: 1970
• Tongue: French
• Weight: 103 KB
• Volume: 11
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89365-x

✦ Synopsis

In the course of our investigations on the photochemistry of a-chloroketones we have photolyzed exo-3-chlorobicyclo[2.2.l~hept-5-en-2-one (1). -Ketone L when photolyzed in methanol (0.05 l4, 1> through a Pyrex filter with Rayonet 3000 1 lamps results in the stereospecific formation of endo-6-carbomethoxybicyclo[3.l.O]h ex-2-ene (2) in greater than 95% yFeLd. The stmcture of 1,was shown to be correct by comparison of the nmr and ir spectra of 2 with an authentic sample.

1 The quantum yield for the formation of 2 was found to be 0.8 using a benzophenone-benehydrol actinometer.2