218965-47-0Relevant academic research and scientific papers
Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant
Kumaraswamy, Gullapalli,Vijaykumar, Swargam,Ankamma, Kukkadapu,Narayanarao, Vykunthapu
, p. 11415 - 11425 (2016/12/16)
The synthesis of regio- and stereoselective aryl substituted α,β-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating dissolved oxygen as a chemical switch for two different reaction pathways. The salient feature of this protocol is the single electron transfer (SET) achieved by irradiation of one of two organic molecules thereby avoiding a sensitizer to form a radical ion pair.
New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides
Redon, Sébastien,Leleu, Stéphane,Pannecoucke, Xavier,Franck, Xavier,Outurquin, Francis
, p. 9293 - 9304 (2008/12/22)
A general method for the preparation of α-phenylselanyl enones is described. Phosphorus ylides react with these α-phenylselanyl enones in a 1,4-addition, leading to cyclopropanes and/or dihydrofurans, depending on the substitution pattern. This unusual reactivity is due to the phenylselanyl moiety, hindering the carbonyl of the enone and making it less prone to 1,2-additions or promoting conjugate addition by electronic effects.
Stereoconservative formation and reactivity of α-chalcogen- functionalized vinyllithium compounds from α-bromo-vinylic chalcogenides
Braga, Antonio L.,Zeni, Gilson,De Andrade, Leandro H.,Silveira, Claudio C.
, p. 595 - 596 (2007/10/03)
Bromine/lithium exchange was performed upon treatment of α-bromo-vinylic chalcogenides with butyllithium in hexane at room temperature to provide α-chalcogen-vinyllithium intermediates quantitatively. Addition of electrophiles to the lithiated compounds g
