Abstract
Unexpected difficulties with Simmons–Smith cyclopropanation of the trimethylsilyl enol ether of exo-tricyclo[3.2.1.02,4]-octan-6-one led to a reexamination of this reaction with the parent norcamphor derivative which under "concentrated" conditions gave ring-expanded allylic ethers in low yield. With the tert-butyldimethylsilyl ethers, however, the allylic product is formed in high yield in the norcamphor and exo-trimethylenenorcamphor (tricyclo[5.2.1.02,6]decan-8-one) systems. The tert-butyldimethylsilyl enol ethers of bicyclo[3.2.1]octan-6-one and nopinone do not undergo ring expansion under similar conditions but the silyl ether of 3-methylenenopinol is a major product in the latter case.
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