64516-63-8Relevant academic research and scientific papers
Conjugate addition of RMgX-3MeLi to α,β-unsaturated amides and α,β-unsaturated carboxylic acids
Kikuchi, Mikiko,Niikura, Satomi,Chiba, Nao,Terauchi, Nahoko,Asaoka, Mono
, p. 736 - 737 (2008/02/09)
In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in good yields. Copyright
Synthetically useful desulfurisation reactions of heteroaryl sulfoxide conjugate adducts
Casey,Gairns,Walker
, p. 1725 - 1728 (2007/10/03)
Efficient desulfurisation reactions of the conjugate addition products derived from 1-methyl-2-imidazolyl and 2-pyridyl sulfoxides have been achieved. Hydrodesulfurisation was effected either by reduction of the sulfoxides to sulfides, followed by treatment with Raney nickel, or more reliably by reaction of either the sulfides or the sulfoxides with nickel boride. Pyrolytic elimination furnished alkenes stereoselectively on heating the sulfoxides to reflux in toluene or chloroform.
Acyl Radicals: Intermolecular and Intramolecular Alkene Addition Reactions
Boger, Dale L.,Mathvink, Robert J.
, p. 1429 - 1443 (2007/10/02)
A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed.Primary alkyl-, vinyl-, and arylsubstituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction.Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally >/= 1 x 106 s-1 with some occuring at rates >/= 3 x 107 s-1.Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical conditions.Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.
Phenyl Selenoesters as Effective Precursors of Acyl Radicals for Use in Intermolecular Alkene Addition Reactions
Boger, Dale L.,Mathvink, Robert J.
, p. 1777 - 1779 (2007/10/02)
The scope of the use of phenyl selenoesters as effective precursors to acyl radicals for use in intermolecular olefin addition reactions is detailed.
