153783-87-0Relevant 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.
Phenacylthio/sulfonyl acetates as synthons: Synthesis and conformational aspects of some 1,4-thiomorpholines Part III
Reddy, D. Bhaskar,Reddy, M. Muralidhar,Reddy, P. V. Ramana
, p. 1018 - 1023 (2007/10/02)
The synthons, phenacylthio/sulfonyl acetates (III and IV) for the synthesis of title compounds VI, VII and VIII have been obtained by two different methods starting from phenacylbromide (I) and thioglycollic acid or from I and thioglycollates.The cyclocon
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.
