22859-16-1Relevant articles and documents
Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry
Bothe, Michael,Furlan, Ricardo L. E.,Orrillo, A. Gastón,Von Delius, Max
supporting information, p. 1988 - 1994 (2019/10/22)
To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Bronsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S, S, S-orthoester exchange over O, O, O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.
Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction
Cui, Fei-Hu,Chen, Jing,Su, Shi-Xia,Xu, Yan-Li,Wang, Heng-Shan,Pan, Ying-Ming
, p. 3950 - 3961 (2017/11/20)
An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2-diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions. (Figure presented.).
Multinuclear NMR study of the solution structure and reactivity of tris(trimethylsilyl)methyllithium and its iodine ate complex
Reich, Hans J.,Sikorski, William H.,Sanders, Aaron W.,Jones, Amanda C.,Plessel, Kristin N.
supporting information; scheme or table, p. 719 - 729 (2009/09/25)
The extreme steric bulk of tris(trimethylsilyl)methyl derivatives (1-X) provides interesting structural and dynamic behavior for study. Dynamic NMR studies on 1-SePh and 1-I showed restricted rotation around the C-Si bonds of each trimethylsilyl groups. A
1-(organoselanyl)perfluoroalkanols: A stable and efficient precursor for organoselenols
Yamamoto, Terahisa,Moriura, Eri,Sawa, Arisa,Yoshimatsu, Mitsuhiro
scheme or table, p. 1046 - 1047 (2009/12/03)
The 1-(organoselanyl)perfluoroalkanols 1, 3, 4, and 10 were successfully prepared and reactions with hexanoyl chlorides to produce the corresponding esters 5, 7, and 8, accompanied by the selenoesters 6 were conducted. The DBU-mediated alkylations of the heptafluorobutanols 4, 10, and the α-p-nitro-benzoate 2 with alkyl halides easily provided alkyl phenyl selenides 9a-9i and 11a-11c in good to high yields. Copyright