Radical reactions of bicyclo[2.2.1]heptan-3-spiro-2′-oxiranes

Add time:07/27/2019    Source:sciencedirect.com

Tributyltin hydride reduction of 2-bromo- and 2-keto-bicyclo[2.2.1]heptan-3-spiro-2′-oxiranes gives ring opening of the oxirane-rings via intermediate 3-(spiro-2′-oxiranyl)bicyclo[2.2.1]heptan-2-yl radicals, whereas reduction of the analogous 2-(thiocarbonyl)imidazolides) [2-(O-CS-Im)] unusually yields the 2-methoxy derivatives and does not proceed by the expected normal fragmentation to yield 3-(spiro-2′-oxiranyl)bicyclo[2.2.1]heptan-2-yl radicals and subsequent ring-opening of the oxirane rings.

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