199456-73-0Relevant academic research and scientific papers
An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
supporting information, p. 3447 - 3452 (2021/05/04)
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
Conformations of 2-alkyl(aryl)thiocyclohexanones
Samoshin,Kudryavtsev,Yartseva,Lutsenko,Zefirov
, p. 1279 - 1281 (2007/10/03)
According to the 1H NMR data, 2-alkyl(aryl)thiocyclohexanones exist mainly as axial conformers. An exception is 2-(2-benzothiazolylthio)cyclohexanone which exists mainly as equatorial conformer due to intramolecular electrostatic interactions.
New approach to the synthesis of dibenzodithia- and benzothiaazacrown ethers via the aromatization of 2-alkylthio(arylthio)-cyclohexanes during bromination
Kudryatsev,Samofin
, p. 106 - 111 (2007/10/03)
A new scheme for the synthesis of dibenzodithiacrown ethers is proposed based on the use of substituted phenol derivatives as intermediates, prepared by aromatization of 2-alkylthio(arylthio)cyclohexanes during bromination. 1,7-Dithia-8,9,17,18-dibenzo-18-crown-6 and 1,10-dithia-11,12,20,21-dibenzo-21-crown-7 without isomers relative to position of the sulfur atoms have been synthesized, and also new thiadiazamacroheterocycles - 1,4,7-trioxa-10,19-dithia-13,16-diaza-12,17-dioxo-8,9,14,15,20,21- tribenzoheneicosane and 1,4,7,10-tetraoxa-13,22-dithia-16,19-diaza-15,20-dioxo-11,12,17,18,23,24- tribenzotetracosane. 1997 Plenum Publishing Corporation.
Preparation and Stability of 1,4-Oxathian-2-ones
Koskimies, Jorma K.
, p. 101 - 108 (2007/10/02)
Several methods of preparation of various substituted 1,4-oxathian-2-ones are described, including the acid-catalyzed ring closure of δ-hydroxy acids, prepared via α-halo ketones or α-halo acids, and the base-catalyzed ring closure of β-haloethyl thioglycolate. 1,4-Oxathian-2-one is completely hydrolyzed in D2O to the hydroxy acid at a rate comparable to the hydrolysis of δ-valerolactone.The rate of the lactonization is estimated to be ca. 100 times smaller in oxathianone than in valerolactone.
