73061-26-4Relevant academic research and scientific papers
Copper-catalyzed aerobic aliphatic C-H oxygenation with hydroperoxides
Too, Pei Chui,Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 1217 - 1225 (2013/07/26)
We report herein Cu-catalyzed aerobic oxygenation of aliphatic C-H bonds with hydroperoxides, which proceeds by 1,5-H radical shift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carboncentered radicals with molecular oxygen.
Grignard reagents: Alkoxide-directed iodine-magnesium exchange at sp 3 centers
Fleming, Fraser F.,Gudipati, Subrahmanyam,Vu, Viet Anh,Mycka, Robert J.,Knochel, Paul
, p. 4507 - 4509 (2008/03/11)
(Chemical Equation Presented) Sequential addition of i-PrMgCl and BuLi to sp3 hybridized iodoalcohols triggers a facile iodine-metal exchange. Intercepting the resulting cyclic Grignard reagents with a slight excess of an electrophile leads to a diverse range of substituted alcohols. The iodine-magnesium exchange strategy is effective with 3-carbon iodoalcohols bearing alkyl substitutents on the carbinol or adjacent carbons and with the chain-extended homolog 4-iodobutan-1-ol.
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.
Functionalized organolithium compounds of DTBB-catalyzed sulfur-lithium exchange
Foubelo, Francisco,Gutiérrez, Ana,Yus, Miguel
, p. 503 - 514 (2007/10/03)
The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1,4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78°C leads to the formation of the corresponding β- or γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t- BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78°C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.
One-Step Annelation. A Convenient Method for the Preparation of Diols, Spirolactones, and Spiroethers from Lactones
Canonne, Persephone,Foscolos, Georges B.,Belanger, Denis
, p. 1828 - 1835 (2007/10/02)
1-(ω-Hydroxyalkyl)cyclopentanols and -cyclohexanols were prepared in one step in high yields from butane-1,4-diyl- and pentane-1,5-diylmagnesium dibromides and lactones in tetrahydrofuran.This method was found to be general and applicable to lactones of any size (β, γ, δ, and ε) and structure whether aliphatic, aromatic, bicyclic, or spirocyclic.Evidently important steric hindrance close to the carbonyl group prevents annelation and attack on the second nucleophilic center of the Grignard reagent.Furthermore, in the case of oxetan-2-one one obtains, in additionto the corresponding diol, products resulting from scission of the C-O bond.The diols by appropriate transformation afford new routes to spirolactones and spiroethers.
