18424-56-1Relevant articles and documents
The vicinal functionalization of olefins: A facile route to the direct synthesis of β-chlorohydrins and β-chloroethers
Swamy, Peraka,Kumar, Macharla Arun,Reddy, Marri Mahender,Naresh, Mameda,Srujana, Kodumuri,Narender, Nama
, p. 26288 - 26294 (2014/07/08)
An efficient and environmentally benign protocol for the synthesis of vicinal chlorohydroxy and chloromethoxy derivatives in a highly regioselective manner from olefins using NH4Cl as a chlorine source and oxone as an oxidant in aqueous acetone and methanol is demonstrated. This methodology offers an additive and metal chloride free approach and is endowed with simple reaction conditions, high yields a broad substrate scope and good functional group tolerance. Moreover, the aromatic substrates with a terminal double bond exhibited merely Markovnikov selectivity, while the internal alkenes show exclusive regiocontrol and low to moderate diastereoselectivity.
Trichloroisocyanuric Acid as a Cohalogenating Reagent: An Efficient Transformation of Alkenes into Chlorohydrins, β-Chloroethers and β-Chloroacetates
Mendonca, Gabriela Fonseca,Sanseverino, Antonio Manzolillo,Mattos, Marcio C. S. de
, p. 45 - 48 (2007/10/03)
The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid (0.34 mol equiv) in alcohols (MeOH, EtOH, i-PrOH, t-BuOH), acetic acid or aqueous acetone, respectively.
A Novel Method for the Conversion of Halide Anion to the Positive Halogen by Nitrobenzenesulfonyl Peroxide. Application to Oxyhalogenation of Olefin
Yoshida, Masato,Mochizuki, Hideki,Suzuki, Takashi,Kamigata, Nobumasa
, p. 3704 - 3706 (2007/10/02)
Bromide and chloride anions could be readily oxidized into positive halogens by treating with p-nitrobenzenesulfonyl peroxide.The positive halogens, thus formed, reacted with olefins to give epihalonium ions, which were trapped by oxygen nucleophiles inter- or intramolecularly to afford oxyhalogenated compounds.