13976-50-6

Upstream product

• 507-09-5 thioacetic acid 
• 78-94-4 methyl vinyl ketone 
• 507-09-5 tiolacetic acid 
• 1115-56-6 1-Bromo-3-methylpentan-4-one 
• 113380-00-0 1,5-Dimethyl-2-thia-6,7-dioxabicyclo<3.2.0>heptane 
• 113379-98-9 4,5-Dimethyl-2,3-dihydrothiophene 

Downstream Products

• 93810-04-9 β-Acetoxy-β-methyl-δ-benzylmercapto-valeriansaeure-ethylester 

Relevant academic research and scientific papers

Dye-Sensitized Photooxygenation of 2,3-Dihydrothiophenes: Formation of Stable 1,2-Dioxetanes from 4,5-Dialkyl-Substituted Derivatives

Singlet oxygen reacts with 4,5-dimethyl- (1a), 4-ethyl-5-methyl- (1b), and 4-isopropyl-5-methyl-2,3-dihydrothiophene (1c) to give 1,2-dioxetanes 2a-c in high yields (> 90 percent). 2a-c represents the first examples of sulfur-substituted dioxetanes that could be isolated.Less than 5 percent of allylic hydroperoxides 3a, 4a, and 3b, identified by their 1H NMR spectra, and less than 5 percent of S-oxides 5a-c were formed in competing ene reactions and sulfoxide-producing steps, respectively.Due to its decreased rigidity, dioxetane 2a is less stable than its oxygen counterpart.Increased flexibility of dioxetanes derived from dihydrothiophenes and dihydrothiopyranes, as compared to those derived from dihydrofurans and dihydropyrans, causes dioxetanes 9 and 16, obtained from 4-carbomethoxy-5-methyl-2,3-dihydrothiophene (8) and 5,6-dimethyl-3,4-dihydro-2H-thiopyran (14), to cleave into dicarbonyl compounds readily at low temperatures.Sulfur-substituted allylic hydroperoxides are also less stable than their oxygen counterparts.Formation of the expected endocyclic allylic hydroperoxides 3a, 3b, and 10 is inferred from the appearance of their H2O2 elimination products, thiophenes 7a, 7b, and 13, respectively.

Reversible generation of metastable enols in the 1,4-addition of thioacetic acid to α,β-unsaturated carbonyl compounds

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.

AN EASY PREPARATION OF SIMPLE SULTINES AND HYDROXYALKANESULFINATE SALTS

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.