50653-82-2Relevant academic research and scientific papers
A metathesis-acylation approach to the bicyclic core of polycyclic poly-prenylated acylphloroglucinols
Schmitt, Stefanie,Feidt, Eva,Hartmann, David,Huch, Volker,Jauch, Johann
, p. 2025 - 2029 (2014)
An approach to a model compound for polycyclic polyprenylated acylphloroglucinols is developed using a ring-closing metathesis approach to give a substituted cyclooctene. This undergoes cyclization via an intramolecular acylation leading to a substituted bicyclo[3.3.1]nonan-9-one related to hyperforin, nemorosone, clusianone, garsubellin A and other members of the polyprenylated acylphloroglucinol. Georg Thieme Verlag Stuttgart · New York.
Mechanistic Aspects of Oxygen Transfer by gem-Dialkylperoxonium Ions
Bloodworth, A. J.,Melvin, T.,Mitchell, John C.
, p. 1078 - 1082 (2007/10/02)
Monocyclic gem-dialkylperoxonium ion 2 has been generated from the reaction of 1-bromo-4-hydroperoxy-4-methylpentane (1) with silver tetrafluoroborate or trifluoroacetate, and related bicyclic ion 4 has been formed from the reaction of 5-hydroxyperoxycyclooctene (3) with N-bromosuccinimide.These species have been shown to oxidize efficiently both dialkyl sulfoxides and methyl phenyl sulfide.Reaction with thianthrene 5-oxide afforded XNu values of 0.10 for 2 and 0.72 for 4, while competition reactions with (p-XC6H4)2SO (X=Me, H, F, and Cl) yielded Hammett ρ values (versus ?) of -0.83+/-0.11 and -1.77+/-0.58.These results indicate that gem-dialkylperoxonium ion salts,R2O+-OH,X-, are electrophilic oxygen transfer reagents, tunable to some extent by choice of R1, R2, and X, but provide no evidence of deprotonation to the corresponding dioxygen ylide under the conditions studied.
