5194-35-4Relevant articles and documents
Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones
Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 873 - 877 (2015/04/14)
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.
γ-Butyltelluro-2-butanol: A route to reactive 1,4-dianion intermediates
Princival, Jefferson L.,De Barros, Simone M. G.,Comasseto, Jo?o V.,Dos Santos, Alcindo A.
, p. 4423 - 4425 (2007/10/03)
γ-Butyltelluro-2-butanol was reacted with 2 equiv of n-butyllithium. Both tellurium/lithium exchange and the proton abstraction reactions took place in a single step and the lithium dianion intermediate efficiently reacted with aldehydes and ketones, producing the corresponding diols.
