2-Mercapto-3- acrylic acid

Treatment of the disulfide (90) with iodine in dioxane under various conditions gives low yields of 5,6-dimethoxy-2,3-dihydrobenzo[6]-thiophene.346 At high temperatures in ethylene glycol a mixture of this compound and the dehydrogenated product, 5,6-dim ethoxy-benzo[6]thiophene, is obtained. These observations demonstrate the importance of the double bond in the side chain of the mercapto-acrylic acids (88) in promoting their cyclization. 

Acrylic acid, -(3-benzo[f>]thienyl)-a -mercapto-reaction with iodine, 4, 764 Acrylic acid, o -cyano-y3-(2-thienyl)-ring opening, 4, 807 Acrylic acid, -formyl-in pyridazinone synthesis, 3, 46 Acrylic acid, furyl-rotamers, 4, 545 synthesis, 4, 658 Acrylic acid, 2-hydroxybenzoyl-chroman-4-one synthesis from, 3, 850 Acrylic acid, 5-(l-propynyl)-2-thienyl-methyl ester occurrence, 4, 909 Acrylonitrile... 

A large number of examples of redox polyelectrolyte monolayers have been reported [42[. Anson described the adsorption of poly(acrylic acid) onto glassy carbon with electrostatic binding of Ru(NH3)6 and Co(NH3)6 ions from solution [43]. Finklea [44] adsorbed poly(4-vinyl-I-methyl-pyridinium methylsulfate) on self-assembled mercapto-undecanoic self-assembled monolayer (SAM) on gold electrodes to... 

Types of compounds are arranged according to the following system hydrocarbons and basic heterocycles hydroxy compounds and their ethers mercapto compounds, sulfides, disulfides, sulfoxides and sulfones, sulfenic, sulfinic and sulfonic acids and their derivatives amines, hydroxylamines, hydrazines, hydrazo and azo compounds carbonyl compounds and their functional derivatives carboxylic acids and their functional derivatives and organometallics. In each chapter, halogen, nitroso, nitro, diazo and azido compounds follow the parent compounds as their substitution derivatives. More detail is indicated in the table of contents. In polyfunctional derivatives reduction of a particular function is mentioned in the place of the highest functionality. Reduction of acrylic acid, for example, is described in the chapter on acids rather than functionalized ethylene, and reduction of ethyl acetoacetate is discussed in the chapter on esters rather than in the chapter on ketones. 

Toxic heavy metals, such as cadmium, lead, and mercury, are sulfur seekers that bind strongly with thiol groups, which is one of the ways in which they interact adversely with biomolecules, including some enzymes. Advantage has been taken of this tendency to use thiols in chelation therapy in heavy metal poisoning. Among the thiols tested for this purpose are meso-2,3-dimer-captosuccinic acid, diethyldimercapto succinate, a-mercapto-P-(2-furyl), and a-mercapto-P-(2-thienyl) acrylic acid.3 The structural formulas for the first two are... 

A similar strategy was reported by Asahi Glass which prepared fluoroacrylic (FA) diblock copolymem used as surface active agents [117]. Acrylates containing perfluorinated groups were telomerized with mercapto acetic acid followed by the condensation of the telomer produced with polypropylene oxide (PPO) to yield PPO-t-PFA diblock copolymers. 

The oxathiocin 771 was synthesized from a-(bromomethyl)acrylic acid and 3-mercapto-l-propanol in the presence of NEt3 to give - [ (3-hydroxy propy I )thio methyl [acrylic acid 792, which by an intramolecular cyclization in presence of NEt3 and 2-chloro-l-methylpyridinium iodide yielded the eight-membered ring in good yield (Scheme 155) <2005ASC1811>. 

Purified mercaptoacetic acid is sold in anhydrous or 85% aqueous forms, most often for subsequent conversion to the esters or to the ammonium, sodium, potassium, or calcium salts. 3-Mercaptopropionic acid is produced from metal hydro sulfides and either acrylic acid or acrylonitrile. Mercaptoethyl tallate is another mercapto-ester used in commercial organotin stabilizers. It is manufactured by a standard esterification of mercaptoethanol and tall oil, a mixture of fatty acids. 

Use of aqueous alkali is sufficient to bring about addition of thiols to unsaturated dicarboxylic acids23 and of mercapto carboxylic acids to acrylic acid.24... 

The synthesis of isomeric thienothiophenes and benzothienothiophenes was successfully carried out starting from thiophenecarbaldehydes and their derivatives. Treatment of 2-mercapto-3-(3-thienyl)acrylic acid (37), prepared in quantitative yield from thiophene-3-carbaldehyde (38) and 2-thioxothiazolidin-4-one (39) through intermediate 40, gave with two equivalents of iodine in dioxane thieno[2,3- )]thiophene-2-carboxylic acid (41) (74SC29). 

Condensation of 73 and related aldehyde 271 with acetoacetate and NH3 afforded 1,4-dihydropyridines 272 [157]. Reaction of 73 with rhodanine followed by basic hydrolysis of 273 led to a-mercapto-p-(5-trifluoromethyl-2-furyl)acrylic acid 274 [158],... 

Mercaptoethyl sulfide, see T-00157 a-Mercapto-j -(2-furyl)acrylic acid, see... 

In the early 1960s, Brannock et al. reported a thermal [2+2] cycloaddition of enamines. Enamines react with a variety of electron-deficient alkenes such as acrylates, nitro-olefines, acetonitriles, vinylsulfones, fumarates, and malei-mides to give aminocyclobutanes [4]. The reaction generally does not require the assistance of an acid catalyst. Narasaka et al. exploited asymmetric thermal [2+2] cycloaddition of vinyl and aUenyl sulfides with electron-deficient alkenes catalyzed by Lewis acid [5]. Yamazaki et al. have reported that a stoichiometric amount of Lewis acid activates [2+2] cycloaddition of vinylselenides with highly electron-deficient olefins [6]. These reactions proceed via a stepwise annulation to give mercapto- and seleno-cyclobutanes, respectively. However, cyclobutane formation from silyl enol ethers, which are one of the most easily prepared ketone... 

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