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Beyond the Dimer and Trimer: Tetraspiro[2.1.2 5 .1.2 9 .1.2 13 .1 3 ] hexadecane‐1,3,5,7‐tetraone—the Cyclic Tetramer of Carbonylcyclopropane
Author(s) -
Sedenkova Kseniya N.,
Averina Elena B.,
Grishin Yuri K.,
Andriasov Kristian S.,
Stepanova Svetlana A.,
Roznyatovsky Vitaly A.,
Kutateladze Andrei G.,
Rybakov Victor B.,
Albov Dmitry V.,
Kuznetsova Tamara S.,
Zefirov Nikolay S.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600140
Subject(s) - chemistry , cyclopropane , dimer , dioxirane , cyclooctane , medicinal chemistry , reactivity (psychology) , trimer , tetramer , methylene , hexadecane , hydrocarbon , organic chemistry , stereochemistry , ring (chemistry) , medicine , alternative medicine , pathology , enzyme , catalysis
Tetraspiro[2.1.2 5 .1.2 9 .1.2 13 .1 3 ]hexadecane‐1,3,5,7‐tetraone 4 , a unique tetraketone containing a cyclooctane core and four spiroannelated cyclopropane moieties, represents the previously unknown cyclotetramer of carbonylcyclopropane. For this purpose oxidation of the parent polyspirocyclic hydrocarbon was examined under various oxidative conditions, and the reactivity of oxidants towards methylene groups of the eight‐membered cycle, activated by adjacent spirocyclopropane rings, was evaluated and contrasted. Whereas the treatment of tetraspirohexadecane with ozone resulted in monooxidation, its reaction with methyl(trifluoromethyl)dioxirane afforded the product of four‐fold oxidation, triketoalcohol 10 . Subsequent oxidation of the latter with Dess–Martin periodinane gave the target tetraketone 4 .