6684-66-8Relevant academic research and scientific papers
ORGANOALUMINIUM REAGENTS INDUCED ISOMERISATION OF 5-HYDROXY-3,3,6-TRIMETHYL-5-HEPTENOIC ACID δ-LACTONE TO 2,2,5,5-TETRAMETHYL-1,3-CYCLOHEXANEDIONE
Tomioka, Hiroki,Oshima, Koichiro,Nozaki, Hitoshi
, p. 99 - 100 (1982)
Treatment of the title lactone and the related δ or ε-lactones with Et2AlSR (R = Et or Ph) gave 1,3-cyclohexanediones or 1,3-cycloheptanediones in excellent yields.
Concerted 1,2-Carbonyl Migration in Organic Synthesis. A Practical Synthesis of Spiro Cyclic 1,3-Diketones
Bach, Robert D.,Klix, Russell C.
, p. 5438 - 5440 (1985)
A general method for the synthesis of α,β-unsaturated cyclic enones is described that involves the α-thioalkylation of cyclic silyl enol ethers in tandem with a low-temperature metaperiodate oxidative dehydrosulfenylation of β-keto sulfoxide.The facile Lewis acid catalyzed acyl migration of a series of α,β-epoxy ketones affords a practical synthesis of cyclic spiro 1,3-diketones.
An unexpected directing effect in the asymmetric transfer hydrogenation of α,α-disubstituted ketones
Soni, Rina,Collinson, John-Michael,Clarkson, Guy C.,Wills, Martin
supporting information; experimental part, p. 4304 - 4307 (2011/10/11)
α,α-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound η6-arene ring in the reduction transition state.
Self-terminating, oxidative radical cyclizations
Dreessen, Tim,Jargstorff, Christian,Lietzau, Lars,Plath, Christian,Stademann, Arne,Wille, Uta
, p. 480 - 497 (2007/10/03)
The recently discovered novel concept of self-terminating, oxidative radical cyclizations, through which alkynes can be converted into carbonyl compounds under very mild reaction conditions using O-centered inorganic and organic radicals as oxidants, is d
Self-terminating, oxidative radical cyclizations of medium-sized cycloalkynones with inorganic and organic oxygen-centered radicals of type XO·: The reaction pathway depends on the nature of X
Wille, Uta,Jargstorff, Christian
, p. 1036 - 1041 (2007/10/03)
The reaction of various inorganic and organic oxygen-centered radicals of type XO· with cyclodec-5-ynone 6 can be used as a mechanistic probe to study the ease with which X· acts as a leaving group in self-terminating, oxidative radical cyclizations. It was observed that when X· has good leaving ability the reaction leads to formation of the bicyclic epoxy ketones 13 and 14, whereas in the other cases a competition between the individual reversible cyclization steps resulted in predominant formation of the spiro ketone 20. The experimental data obtained lead to the suggestion that vinyl radicals could rearrange through 1,2-group migrations.
LEWIS ACID CATALYZED REARRANGEMENTS OF STUCTURALLY RELATED α,β-UNSATURATED EPOXY KETONES AND OXIMES. A COMPLEMENTARY APPROACH TO THE SYNTHESIS OF ISOMERIC 1,4-DIKETOSPIRO ALKANES.
Bach, Robert D.,Tubergen, Mark W.,Klix, Russel C.
, p. 3565 - 3568 (2007/10/02)
Lewis acid catalyzed rearrangement of α,β-epoxy oximes proceeds by oxirane cleavage α to the oxime moiety with an attendant pinacol type alkyl migration to the resonance stabilized carbenium ion at Cα affording a 1,3-diketo-monoxime.
