Abstract
Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5- exo- trig mode of cyclization rather than 6- endo- trig mode of cyclization takes place whereas in case of acetylenic side chain we observed 6- endo cyclization.
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