Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
作者:Manoj K. Agrawal、Subbarayappa Adimurthy、Bishwajit Ganguly、Pushpito K. Ghosh
DOI:10.1016/j.tet.2009.01.095
日期:2009.4
halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br−/BrO3− and I−/IO3− reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br−/BrO3− and I−/IO3−, respectively. Of the two reagents, I−/IO3− was established to be the preferred reagent for vicinal functionalization of linear alkenes and
Electrochemical regioselective azidoiodination of alkenes
作者:Wei-qing Yan、Meng-ying Lin、R. Daniel Little、Cheng-Chu Zeng
DOI:10.1016/j.tet.2016.12.058
日期:2017.2
An efficient electrochemical approach to the vicinal iodoazides has been developed through constant current electrolysis of alkenes with NaN3 and NaI in methanol. The reaction is proposed to proceed via a cyclic iodonium intermediate and thereby gives Markovnikov addition products exclusively.
IPy2BF4-Mediated Rearrangements of 1,2-Difunctionalized Compounds and Olefins
作者:Francisco J. Fañanás、Mónica Álvarez-Pérez、Félix Rodríguez
DOI:10.1002/chem.200500070
日期:2005.10.7
Acetal derivatives are easily obtained from 1,2-difunctionalizedcompounds by a new reaction mediated by IPy2BF4 with a mechanism based on a 1,2-migration of aryl or alkyl groups. A new oxidative rearrangement reaction of olefins is also described. Moreover, when this metal-free protocol is applied to cyclic olefins, interesting ring-contraction reactions are observed. The new methodologies described