Synthesis of pentacyclo [4.3. 0.02, 5.02, 8.04, 7] nonane (homocubane) and some of its derivatives

GL Dunn, VJ DePasquo…

Index: Dunn,G.L. et al. Journal of Organic Chemistry, 1968 , vol. 33, # 4 p. 1454 - 1459

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Citation Number: 42

Abstract

prepared8-10 from the stable tetrachlorocyclopentadi-enone ketals. The known tetrachloro ketone 7, first prepared by Yates and Eatonl9 provided a convenient starting point. The intermediate polyhalohomocubanes obtained by this sequence may then be dehalogenated to give the required product. Of the two approaches, the pathway outlined in Scheme I was the more satisfactory. Bromo ketone 1 was prepared by bromination of 2-cyclopentenone ...