Synthesis and rearrangement of strained cage molecules

WG Dauben, CH Schallhorn…

Index: Dauben,W.G. et al. Journal of the American Chemical Society, 1971 , vol. 93, # 6 p. 1446 - 1452

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Citation Number: 38

Abstract

Abstract: The preparation of cis-9, 10-dicarbomethoxypentacyclo [4.4. O. O2~ 5. O3~ 8. O4~ 7ldecane (5, the 1, l'-bishomocubane structure) was effected by the sensitized irradiation of diene diester 4. Photoproduct 5 was converted to bishomocubanedione 11 by a series of reactions involving saponification, bisoxidative decarboxylation, hydroboration, and two oxidations. The diketone 11, via the diazo ketone 12, was photochemically ring contracted ...