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Direct Oxidation of Cyclopropanated Cyclooctanes as a Synthetic Approach to Polycyclic Cyclopropyl Ketones
Author(s) -
Sedenkova Kseniya N.,
Andriasov Kristian S.,
Stepanova Svetlana A.,
Gloriozov Igor P.,
Grishin Yuri K.,
Kuznetsova Tamara S.,
Averina Elena B.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701671
Subject(s) - cyclooctane , chemistry , cyclopropane , oxidizing agent , cycloalkane , dioxirane , reactivity (psychology) , organic chemistry , eucalyptol , cyclopropanation , ring (chemistry) , medicinal chemistry , cyclohexane , catalysis , medicine , alternative medicine , pathology , chromatography , essential oil
A series of polycyclic hydrocarbons containing cyclopropane moieties 1,2‐annelated or spiro‐condensed with a cyclooctane ring were investigated under oxidative conditions. Four oxidizing systems (O 3 on SiO 2 , a dioxirane derived from trifluoroacetone, CrO 3 , and RuO 4 , generated in situ), were tested to evaluate and compare their reactivity and usefulness. RuO 4 was found to be the best of them, considering its oxidative power together with the simple operating procedure. Conditions for the specific oxidation of polycyclic hydrocarbons were found. New cyclooctane derivatives containing cyclopropyl carbonyl moieties were obtained.