Homolytic Reactions of Homocubane and Basketane: Rearrangement of the 9-Basketyl Radical by Multiple. beta.-Scissions

GT Binmore, EW Della, GM Elsey…

Index: Binmore, Gavin T.; Della, Ernest W.; Elsey, Gordon M.; Head, Nicholas J.; Walton, John C. Journal of the American Chemical Society, 1994 , vol. 116, # 7 p. 2759 - 2766

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Citation Number: 11

Abstract

Abstract: Methods are described for the synthesis of 9-hydroxy-and 9-bromopentacyclo [4.3. 0.02~~. 0~~~. 04~ 7] n0nane (homocubane derivatives) and for the same derivatives of pentacyclo [4.4. 0.02~~. 03~~. 04J] dccane (basketane). The 9-homocubyl and 9-basketyl radicals generated from these precursors were observed by EPR spectroscopy. In spite of their very large strain energies, both radicals rearranged extremely slowly, and ...