54278-24-9Relevant academic research and scientific papers
Reversible generation of metastable enols in the 1,4-addition of thioacetic acid to α,β-unsaturated carbonyl compounds
Hintermann, Lukas,Turo?kin, Aleksej
supporting information, p. 11345 - 11348 (2013/02/25)
Addition of thioacetic acid to reactive α,β-unsaturated carbonyl compounds like acrolein or crotonaldehyde in acetone-d6 generates metastable (E)-and (Z)-1-alkenols, which tautomerize slowly at ambient temperature. The 1,4-addition of thioacetic acid and crotonaldehyde to (Z)-3-(acetylsulfanyl)-1-propen-1-ol is reversible with Keq = 5.5 ± 0.5 L/mol. A concerted, cyclic 1,4-addition mode is proposed to explain the preferred (Z)-stereoselectivity in lower polarity, nonprotic solvents.
A new autocatalytic thioacetate-enal addition reaction: A Michael addition or not?
Ilyashenko, Gennadiy,Whiting, Andrew,Wright, Allen
body text, p. 1818 - 1825 (2010/11/19)
Rather than proceeding through a Michael-type or 1,4-addition, thioacetic acid adds across unsaturated aldehydes in an autocatalytic manner and involving a double exotherm, as demonstrated by both adiabatic and reaction calorimetry. NMR studies show that an intermediate acyl-thio-hemiacetal is involved and that the product continues to react competitively with thioacetic acid.
NOVEL 1,3-OXATHIANE COMPOUNDS AND THEIR USE IN FLAVOR AND FRAGRANCE COMPOSITIONS
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Page/Page column 3, (2010/05/13)
The present invention relates to novel 1,3-oxathiane compounds represented by Formula I: wherein R is selected from the group consisting of ethyl, butyl, propyl, and (methylthio)ethyl, and their uses to enhance a flavor or fragrance composition.
AN EASY PREPARATION OF SIMPLE SULTINES AND HYDROXYALKANESULFINATE SALTS
King, J. F.,Rathore, Rajenda
, p. 2763 - 2766 (2007/10/02)
In accord with mechanistic prediction a one-pot, two-stage, controlled chlorination-hydrolysis of HO(CH2)nSH gave the sultine when n=3 or 4, and the polymeric sulfinic ester when n=5 or 6; alkaline hydrolysis of either product yielded the corresponding sodium ω-hydroxy-1-alkanesulfinate.
