Sulfinic Acids and Derivatives

Abstract

The article contains sections titled: 1. Introduction 2. Properties 3. Preparation of Sulfinic Acids and their Salts 3.1. Reduction of Sulfonic Acid Derivatives 3.2. Sulfination with Sulfur Dioxide 3.3. Oxidation of Thiols 3.4. Nucleophilic Cleavage of Sulfones and Related Compounds 4. Reactions of Sulfinic Acids and their Derivatives 4.1. Alkylation of the Sulfinate Anion 4.2. Addition of Sulfinic Acids to Multiple Bonds 4.3. Redox Reactions of Sulfinic Acids 5. Sulfinic Acid Derivatives 5.1. Sulfinyl Chlorides 5.1.1. Preparation 5.1.2. Reactions 5.2. Sulfinic Acid Esters 5.2.1. Preparation 5.2.2. Reactions 5.3. Thiosulfinic Acid Esters 5.4. Sulfinic Acid Amides 6. 1‐Hydroxyalkanesulfinates 6.1. Properties 6.2. Production 6.3. Quality Specifications, Analysis 7. Formamidinesulfinic Acid 7.1. Properties 7.2. Production 8. Industrial Uses of Sulfinic Acids and their Derivatives 9. Toxicology

High mortality in geese associated with feeding tofu skin waste in Hebei Province, China

“…This eventually caused goose poisoning, which also suggested that there may be cases where individual farmers violated animal welfare principles and used illegal feed to raise animals. ), which is also known as sodium formaldehyde sulfoxylate or sodium oxymethylene sulfoxylate) [1] is widely used as an industrial bleaching agent in the printing and dyeing industries [2,3]. As it is suspected to be carcinogenic, its addition to human and animal feed has been banned in many countries, including China [4].…”

Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

“…Aryl and heteroaryl [(het)Ar] sulfinate salts are useful and versatile synthetic intermediates that provide access to structural motifs of relevance to numerous fields of chemistry; sulfones, sulfonamides, and structures arising from C–C bond formation, such as Ar–(het)Ar, Ar–COR, and Ar–CN, can all be accessed from a common sulfinate intermediate (Figure ). In particular, sulfinates are among the intermediates of choice in drug discovery where analogue generation based on versatile synthetic intermediates helps promote rapid exploration of structure–activity relationships (SAR) .…”

“…Indeed, such an approach allows for the efficient synthesis of analogues containing sulfone and sulfonamide functionalities which, as illustrated by the medicines bicalutamide (Casodex) and sildenafil (Viagra), are two pharmacophores often found in therapeutic agents (Figure ). However, the scope for using sulfinates as intermediates in synthesis has been limited by their modest commercial availability (∼200 compounds) and the practicality of existing preparative methods used to access them. , As a result, there remains a need to develop novel synthetic transformations that will allow direct access to aryl and heteroaryl sulfinate salts from a large pool of readily available reactants.…”

“…The reaction did not proceed in the absence of a catalyst or hydrogen donor source, and among the ones we tested, sodium formate gave the best results. We used potassium metabisulfite as a source of SO 2 , as it offers the advantage of buffering the pH of the reaction mixture, thus minimizing any risk of decomposition of the sulfinate by disproportionation of the corresponding sulfinic acid . Based on all of the above observations, we selected Pd(OAc) 2 /PPh 3 /phen in the presence of K 2 S 2 O 5 , NaO 2 CH, and TBAB in DMSO at 70 °C as general conditions to use in further evaluating the scope of the transformation.…”

Palladium‐Catalyzed Three‐Component Diaryl Sulfone Synthesis Exploiting the Sulfur Dioxide Surrogate DABSO

“…This reflects the very limited commercial availability of sodium sulfinates, perhaps as a result of impractical or limited synthetic routes. Organometallic addition to sulfur dioxide gas [12] (followed by cation exchange) and reduction of the sulfonyl chloride [12,13] are two such examples, but both have shortcomings such as the harsh conditions associated with sulfonyl chloride formation or the use of toxic gaseous sulfur dioxide. Taken together, these limitations present a clear mandate for the development of a more general, modular synthesis of sulfones, with the versatility to allow ready variation of both groups attached to the SO 2 linker.…”