6626-15-9Relevant articles and documents
Regioselective bromination of arenes mediated by triphosgene-oxidized bromide
Xu, Yingzhou,Hu, Dufen,Zheng, Hui,Mei, David,Gao, Zhaobo
supporting information, (2019/08/30)
This article first time describes triphosgene (BTC) as an oxidant while the non-toxic and easy-to-handle potassium bromide (KBr) as the source of bromine to the bromination reaction of aromatic substrates. The novel brominating protocol gives excellent para-regioselectivity of the alkoxyl/hydroxyl arenes and high yield, offering good potential of commercial scale applications. The mechanism of “Triphosgene oxidize bromide” was proposed.
Practical regioselective halogenation of vinylogous esters: Synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols
Chen, Xiaohong,Liu, Xiaoguang,Martinez, Jenny S.,Mohr, Justin T.
, p. 3653 - 3665 (2016/06/06)
A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology to access polyhaloresorcinols is also reported. These methods create useful functionalized building blocks for further synthetic applications.
Enantioselective synthesis, stereochemical correction, and biological investigation of the rodgersinine family of 1,4-benzodioxane neolignans
Pilkington, Lisa I.,Barker, David,Wagoner, Jessica,Polyak, Stephen J.
supporting information, p. 1046 - 1049 (2015/03/30)
The enantioselective synthesis and chiroptic analysis of all members of the rodgersinine family of 1,4-benzodioxane neolignans has been achieved. ECD spectra and optical rotation analysis determined that the previously published stereochemistry of trans-rodgersinines A and B was incorrect. The cis-rodgersinines A and B did not follow the model ECD study commonly used to assign the absolute stereochemistry of 1,4-benzodioxane natural products. This finding has implications on the absolute stereochemistry of other natural products of this type. Additionally, the rodgersinines were found to have anti-HCV activities.