105785-75-9Relevant academic research and scientific papers
Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes
Tang, Xiaoping,Chapman, Charlotte,Whiting, Matthew,Denton, Ross
supporting information, p. 7340 - 7343 (2014/07/07)
The development of the first redox-free protocol for the Mitsunobu reaction is described. This has been achieved by exploiting triphenylphosphine oxide-the unwanted by-product in the conventional Mitsunobu reaction-as the precursor to the active P(v) coupling reagent. Multinuclear NMR studies are consistent with hydroxyl activation via an alkoxyphosphonium salt.
The Mechanism of the Mitsunobu Azide Modification and the Effect of Additives on the Rate of Hydroxyl Group Activation
Afonso, Carlos M.,Barros, M. Teresa,Godinho, Licio S.,Maycock, Christopher D.
, p. 9671 - 9678 (2007/10/02)
The Mitsunobu azide modification has been studied by NMR using a hindered alcohol and the principle intermediates involved have been tentatively identified.The accelerated hydroxyl group activation in the presence of hydrazoic acid or of catalytic quantities of phenol gives us an insight into the reactivity of some of the intermediates involved in these reactions.
Bis(neopentyloxy)triphenylphosphorane: A Versatile, Nonalkylating Cyclodehydration Reagent
Kelly, Jeffery W.,Evans, Slayton A.
, p. 5490 - 5492 (2007/10/02)
Bis(neopentyloxy)triphenylphosphorane (BNTP; 31P δ -58.3) is prepared in 48percent yield by reaction of 2 equiv of lithium neopentoxide with dibromotriphenylphosphorane in anhydrous dichloromethane from -78 to 25 deg C.BNTP smoothly converts a variety of diols, 2-aminoethanol, and 4-mercaptobutanol to the corresponding heterocycles in excellent yields (>95percent) by 13C and 31P NMR analysis.
