2230-77-5Relevant articles and documents
Chirality transfer through sulfur or selenium to chiral propellers
Skowronek, Pawel,cianowski, Jacek,Pacula, Agata J.,Gawroski, Jacek
, p. 69441 - 69444 (2015/09/01)
The mechanism of chirality transfer from a chiral alkyl substituent to a trityl moiety through sulfur or selenium atoms is analysed and discussed on the basis of ECD measurements, DFT structure and ECD spectra calculations. It is shown that the presence o
Clarification of the stereochemical course of nucleophilic substitution of arylsulfonate-based nucleophile assisting leaving groups
Braddock, D. Christopher,Pouwer, Rebecca H.,Burton, Jonathan W.,Broadwith, Phillip
supporting information; experimental part, p. 6042 - 6049 (2009/12/24)
(Chemical Equation Presented) Secondary alcohols modified as tosylates, PEG-sulfonates, or quisylates undergo inversion of configuration at the reacting center when treated with lithium halide in acetone at reflux, where the PEG-sulfonates and quisylates are substantially more reactive. In sterically hindered cases, elimination is a competing process. In contrast, when treated with TiCl4, simple secondary sulfonates give chloride products with partial inversion of configuration. Any observed retention of configuration in a given alkyl sulfonate substrate under these conditions is likely due to neighboring group participation or diastereoselective attack on a carbocation (or ion pair) rather than an SNi mechanism.
An efficient and selective tosylation of alcohols with p-toluenesulfonic acid
Das, Biswanath,Reddy, V. Saidi,Reddy, M. Ravinder
, p. 6717 - 6719 (2007/10/03)
Silica chloride has been found to be an efficient catalyst for facile tosylation of alcohols directly with p-toluenesulfonic acid in methylene chloride under reflux. The process is associated with selective tosylation of secondary alcohols over primary al
