Organic Sulfur Derivatives. II.² Sulfides, Sulfoxides and Sulfones from Thiols and 10-Undecenoic Acid

Abstract

Sulfur Derivatives from Thiols and 10-Undecenoic Acid 4235 sodium dissolved in 10 ml. of absolute ethanol was added 3.98 g. (0.0195 mole) of diethyl formamidomalonate. To this solution was added 4.92 g. (0.0195 mole) of VHd in 15 ml. of ethanol. The mixture was refluxed for 5 hr. and then evaporated to dryness under reduced pressure. One hundred ml. of water was added with stirring, the solid removed by filtration and recrystallized from ethanol; yield 4.6 g. (63%), m.p. 236-240°. A sample was recrystallized from dioxane-heptane for analysis, m.p. 239-240°.^-Sulfamylphenylalanine (VII).-The amino acid hydrochloride was obtained by refluxing 21 g. (0.056 mole) of Vile with 200 ml. of concentrated hydrochloric acid for 5 hr. The solution was evaporated to dryness under reduced pressure. The hydrochloride salt was dissolved in 100 ml. of water and the solution passed through a column oi Duolite A-2 ion-exchange resin to obtain the free amino acid. The resulting solution was evaporated to 125 ml. under reduced pressure and 100 ml. of acetone added. The solution was cooled overnight and the crude product was collected; yield 10.5 g. (76%), m.p. 248-249°dec. A sample was recrystallized from water-acetone for analysis, m.p. 251-252°dec. Kankakbb, Illinois

Novel Castor Oil‐Derived Block Copolymers as Promising Candidates for Biological Applications: Biorelevant and Biocompatible

“…We carried out the mercaptoethanol addition to obtain the TEHA under UV‐irradiation at room temperature in presence of DMPA as photoinitiator (Scheme ). The reaction has been previously described, to proceed moderately rapidly at temperatures below 100 °C, under free‐radical conditions, with the assistance of ultraviolet light . The successful synthesis of TEHA was determined using 1 H‐NMR spectroscopy, that showed full conversion of the double bonds by the disappearance of the vinylic and allylic hydrogen signals at 5.35 and 2.00 ppm, respectively, in Figure a.…”

Kinetics of the Addition Reactions of Thiobenzoic Acids to Styrenes or Ethynylbenzenes as the Model of Polyaddition. Study on the Rate-Determining Step and Substituent Effect

“…Similar addition reactions have been reported with carbothioic acid (thiol acid) compounds. 1 For example, Koening et al 2 synthesized thioesters by the radical addition reaction of thioacetic acid to vinyl compounds. The analogous reaction with acetylenes gave the 1 : 1 and 2: 1 adducts with thioacetic acid and acetylenes.…”

Fully biobased triblock copolyesters from l-lactide and sulfur-containing castor oil derivatives: Preparation, oxidation and characterization

“…Synthesis of this monomer was previously described by simply stirring mercaptoethanol and 10-undecenoic acid for 1.5 h at 60 C. Moreover, reaction has also been described to take place when UV irradiated [29]. We carried out the mercaptoethanol addition to obtain the thioether-containing uhydroxyacid (TEHA, Scheme 1) under irradiation at room temperature in presence of 2,2-dimethoxy-2-phenylacetophenone (DMPA) as photoinitiator.…”