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Chemistry of Cage‐shaped Hydrocarbons. The Oxidation of Heptacyclo[6.6.0.0 2,6 .0 3,13 .0 4,11 .0 5,9 .0 10,14 ]tetradecane
Author(s) -
Chow Tahsin J.,
Wei ChinChuan,
Wu TungKung
Publication year - 1994
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199400116
Subject(s) - chemistry , iodine , photodissociation , cage , regioselectivity , fission , photochemistry , medicinal chemistry , organic chemistry , neutron , catalysis , nuclear physics , physics , mathematics , combinatorics
Oxidative ring opening reactions enabled disassembly of the cage structure of the title compound. Stepwise oxidations were achieved through radical intermediates using lead tetracetate and iodine. The regioselectivity of bond fission is rationalized by comparing the relative strains of each bond. Multiple cleavages of C‐C bond were accomplished by photolysis with HgO and iodine under UV. The oxidative effect of Ce(IV) ion on a cage‐shaped diketone is examined. New skeletons of polyquinanes are obtained from these reactions.