74947-79-8Relevant academic research and scientific papers
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.
Thiourea catalysis of NCS in the synthesis of β-chloroethers
Bentley, Paul A.,Mei, Yujiang,Du, Juan
, p. 2653 - 2655 (2008/09/19)
Thiourea catalysis of olefin chlorination with NCS in an alcohol gives β-chloroethers with a very fast reaction of high yield.
Electrophilic Additions to Indene and Indenone: Factors Effecting Syn Addition
Heasley, Gene E.,Bower, Timothy R.,Dougharty, Kent W.,Easdon, Jerome C.,Heasley, Victor L.,et al.
, p. 5150 - 5155 (2007/10/02)
The electrophiles bromine, bromine chloride, chlorine, acetyl hypochlorite, and acetyl hypobromite all yield substantial cis addition product by reaction with indene (1) in aprotic solvents, showing that the direct syn collapse of ion pairs obtained from bromine and similar electrophiles is readily possible.The cis to trans ratios with the halogens (but not with the acyl hypohalites) vary with solvent polarities.In the low-polarity solvents (hydrocarbons and carbon tetrachloride) much more syn addition occurs at high halogen concentration.Syn addition of the above electrophiles to 1 as well as methyl hypobromite and methyl hypochlorite was also observed in methanol and acetic acid, with the exception of bromination in methanol where only the trans-dibromide was obtained.Bromine and bromine chloride addition to indenone (20) yielded only the trans-dihalides, suggesting that a neighboring keto group stabilizes the bridged bromonium ion.Chlorination of 20 was not stereospecific but yielded more trans-dichloride than did chlorination of 1.
