52183-00-3Relevant articles and documents
Electrochemically Enabled Carbohydroxylation of Alkenes with H2O and Organotrifluoroborates
Xiong, Peng,Long, Hao,Song, Jinshuai,Wang, Yaohui,Li, Jian-Feng,Xu, Hai-Chao
supporting information, p. 16387 - 16391 (2018/11/23)
Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electrochemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.
Retropinacol/cross-pinacol coupling reactions - A catalytic access to 1,2-unsymmetrical diols
Scheffler, Ulf,Stoesser, Reinhard,Mahrwald, Rainer
supporting information, p. 2648 - 2652,5 (2012/12/12)
A new concept to access unsymmetrical 1,2-diols with high yields is reported. This new methodology is based on a retropinacol/cross-pinacol coupling process. This transformation is characterized by its operational simplicity and very mild reaction condi tions.
Benzophenone-Photosensitized Reactions of Xanthinic Compounds. A Mechanistic Study
Murgida, Daniel H.,Aramendia, Pedro F.,Erra-Balsells, Rosa
, p. 487 - 494 (2007/10/03)
Photosensitized reaction of xanthinic compounds (XH) as caffeine (CF), theobromine (TB) and theophylline (TF) by benzophenone (BZ) in ethanol solution was investigated. In the three cases four main reaction products (benzopinacol; diphenylcarbinol; 1,1-diphenyl-1,2-propanediol and 8-[1-(1-hydroxyethyl)] xanthine) were identified and then characterized by melting point, 1H NMR, 13C NMR and mass spectrometry. The quenching of triplet BZ by the three XH was detected and a thorough kinetic analysis was performed. Caffeine produces mainly physical quenching, while TF reacts by N-H hydrogen abstraction. For TB both mechanisms are operative. Heats of reactions were calculated for chosen reactive steps of the mechanism by the PM3 method. They provide additional support to the proposed reaction scheme. We demonstrate that the mechanism leading to XP formation does not proceed through the X? radical directly obtained by H abstraction. An alternative reaction path through an intermediate radical originated on the addition of ethanol radical to XH is proposed. Redox potentials for the oxidation of XH were estimated by cyclic voltametry and by using the Rehm-Weller equation the redox quenching of triplet BZ by XH was discarded.