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Stereoselective addition of singlet oxygen to 8-isopropylidene-tricyclo[3.2.1.02,4]octane derivatives

✍ Scribed by Keiji Okada; Toshio Mukai

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
213 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sunnnary: Singlet oxygen adds stereoselectively to 8-isopropylidenetricyclo[3.2.1.02y4]octane. The T-orbital distortion and the secondary orbital interaction are discussed in order to explain the observed stereoselectivity. Recently it has been reported by two groups 2,3 that singlet oxygen adds stereoselectively to 7-isopropylidenenorbornene derivatives (a where the aorbital distortion of the exocyclic double bond seems to take an important role. In this connection, we wish to report the photooxidation of 8-isopropylidenetricycloC3.2.1.0 2y4]octane (A), which contain a cyclopropane ring instead of the double bond ofA When a solution of&in acetonitrile or acetone was photooxidized by irradiation with a 500W Tungsten-Brom lamp in the presence of methyleneblue as a sensitizer, followed by the reduction with dimethylsulfide in methanol! a pair of alcohols, anti-(2

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