167558-24-9Relevant academic research and scientific papers
Examination of P-OR bridging bond orders in phosphate monoesters using 18O isotope shifts in 31P NMR
Sorensen-Stowell, Kerensa,Hengge, Alvan C.
, p. 4805 - 4809 (2005)
Evidence indicates that phosphate monoesters undergo hydrolysis by a loose transition state with extensive bond fission to the leaving group. It has been proposed that part of the high dependence of the rate on the leaving group pKa (βlg/
The first general route for efficient synthesis of 18O labelled alcohols using the HOF·CH3CN complex
Gatenyo, Julia,Vints, Inna,Rozen, Shlomo
supporting information, p. 7379 - 7381 (2013/09/23)
A mild and very efficient method for converting boronic acids to alcohols has been developed using the acetonitrile complex of hypofluorous acid HOF·CH3CN. Employing 18O-labeled water results in alcohols containing a heavy oxygen isotope. The reactions were performed at room temperature, within a few minutes and in excellent yields.
Transesterification for synthesis of carboxylates using aldehydes as acyl donors via C-H and C-O bond activations
Bao, Yong-Sheng,Chen, Chao-Yue,Huang, Zhi-Zhen
, p. 8344 - 8349,6 (2020/10/15)
A new type of transesterification between aryl, heteroaryl, alkyl N-heteroarene-2-carboxylates and various aldehydes by C-H and C-O bond activations has been developed for the synthesis of versatile carboxylates. A possible mechanism containing oxidative addition of acyl-O bond in parent ester and radical cleavage of sp2 C-H bond in aldehyde is proposed.
Chemistry of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl radicals. Migration reactions: Scope and stereoselectivity of β-(phosphatoxy)alkyl rearrangement. Mechanism of β-(phosphatoxy)alkyl and β-(acyloxy)alkyl migration
Crich, David,Yao, Qingwei,Filzen, G. Fredrick
, p. 11455 - 11470 (2007/10/03)
An in depth study of the mechanism of the β-(phosphatoxy)alkyl radical migration is presented. Examples are presented which define the scope and limitations of the migration and show that, in certain cases, it is highly stereoselective. It is shown that phosphoranyl radicals are not intermediates in this rearrangement. A series of experiments with stereochemically-, 18O-, and deuterium-labeled probes indicate that the migration is intramolecular, proceeds through competing 1,2- and 2,3-pathways, and does not involve fragmentation to a cage pair followed by recombination. The deuterium-labeled probe is also applied to the β-(acyloxy)alkyl migration with the same result. The changing proportions of 1,2- and 2,3-shifts in going from the β-(phosphatoxy)alkyl to the β-(acyloxy)alkyl migration are discussed in terms of the conformational equilibria of the two different esters and the Curtin-Hammett principle.
