Photochemical cycloaddition of 2-acetoxypent-2-en-1-ones to 1,1-diethoxyethylene and formation of bicyclo [2,2,1] heptane from the adduct

✍ Scribed by Takeshi Matsumoto; Haruhisa Shirahama; Akitami Ichihara; Shohei Kagawa; Sojiro Matsumoto

• Book ID: 104239953
• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 177 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88627-5

✦ Synopsis

The present study of the photochemical cycloaddltlon o? enol acetates of cyclic 1,2-dlketones to l,l-dlethoxyethylene has been InItIated with the hope of applioatlon to the synthesis 2 of some sesquiterpenes, I.e. Illudol etc.3. There Is little known concerning the stereoeelectIvIty and orlentatlonal mode of the cycloaddItIon4 to dlosphenol acetates. 0 AC 9 R 9 F?=c* -lL ..$ :?b lzto R=H 2 R"=ys 3 S Compounds 1,2 and 1 were prepared according to the known procedures. 5 z+ Irradiation of a solution of $/in 1,1-diethoxyethylene for 3 hr with a 75 W high pressure murcury lamp (Pyrex filter) under nitrogen led to an oily product, b.p. 114-118;/7mmHg, which, after purification by preparative gas chromatography,