Once the tetradeuterated cyclopentanone has been prepared, functional group transformations areemployed to convert it to the desired products.(a)Reduction of the carbonyl group can be achieved by using any of the customary reagents.(b)Acid-catalyzed dehydration of the alcohol prepared in part (a) yields the desired alkene.(c)Catalytic hydrogenation of the alkene in part (b) yields cyclopentane-1,1,3-d3.(d)Carbonyl reduction of the tetradeuterated ketone under Wolff–Kishner conditions furnishesthe desired product.Alternatively, Clemmensen reduction conditions (Zn, HCl) could be used.18.28(a)Hydroformylation converts alkenes to aldehydes having one more carbon atom by reactionwith carbon monoxide and hydrogen in the presence of a cobalt octacarbonyl catalyst.(b)
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This note was uploaded on 09/28/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.