2,2-Bis(phenylsulfonyl)ethyl sulfides as efficient precursors of sulfenic acids (original) (raw)
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Recent Advances and Perspectives in the Chemistry of Sulfenic Acids
Current Organic Chemistry, 2007
This review (56 references) provides a comprehensive survey of the literature on sulfenic acid chemistry from 1990 through June 2006, focusing the attention on salient aspects of their structures and involvement in organic processes. Even if the majority of known sulfenic acids cannot be isolated, some stable ones have been obtained, and their study helped dramatically the comprehension of chemical and physical properties of all sulfenic acids and indirectly of the role that Cys-SOHs play in protein biochemistry. Many papers have been published in the last fifteen years about the sulfenic acid intermediacy in organic chemistry. Once generated, they can be involved in intra-and intermolecular additions to unsaturated molecules. Few examples of sulfenic acid addition to double bonds have been recently described and most of them are intramolecular processes, whereas the addition of enantiopure sulfenic acids onto carbon-carbon triple bonds has been widely exploited in the synthesis of vinyl sulfoxides to be used in many stereoselective transformations. The thermic -elimination from sulfinyl precursors is a way to generate sulfenic acids but it has been also used for removing the sulfinyl moiety from organic molecules and forming double bonds with controlled stereochemistry. Some significant applications of extrusion processes are also described in the present review.
Efficient Synthesis of Unsymmetrical Disulfides through Sulfenic Acids
European Journal of Organic Chemistry, 2009
Keywords: Sulfur / Selenium / Sulfenic acids / Alkenes / Michael addition A general procedure for the synthesis of α-(phenylseleno)sulfinyl and -sulfonyl alkenes has been described. 1-(Phenylseleno)ethenyl sulfoxides were prepared by the syn-addition of in situ-generated sulfenic acids on to the triple bond of suitably substituted (phenylseleno)acetylenes. 1-(Phenylseleninyl)ethenyl sulfones were obtained by further oxidation of their sulfinyl analogues. The mild conditions of the sulfenic acid/(phenylseleno)alkyne syn-addition and its stereospecificity and regioselectivity allowed us to obtain elec-
2019
A large variety of organosulfur compounds have been shown to having diverse biological effects such as anti-oxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.
Sulfinate derivatives: dual and versatile partners in organic synthesis
Org. Biomol. Chem., 2014
Sulfinic acids and their salts have recently emerged as versatile coupling partners to efficiently access a wide variety of hetero-and carbocyclic compounds, under relatively mild conditions. Their growing importance is attributable to their dual capacity for acting as nucleophilic or electrophilic reagents. This report summarizes recent advances in the preparation and use of sulfinates in organic synthesis.
One-Pot Parallel Synthesis of Alkyl Sulfides, Sulfoxides, and Sulfones
A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H 2 O 2 or H 2 O 2 −(NH 4) 2 MoO 4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30−300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures. KEYWORDS: one-pot parallel synthesis, alkylation of thiourea, alkyl chlorides, oxidation of alkyl sulfides, ammonium molybdate
Synthesis of sulfides under solvent- and catalyst-free conditions
Monatshefte für Chemie - Chemical Monthly, 2009
A simple, highly efficient, and green protocol has been developed for preparation of sulfides from alkyl or aryl thiols and benzyl-, allyl-, t-butyl, and adamantyl halides under solvent-and catalyst-free conditions.
RSC Advances, 2012
A general, mild, convenient and environmentally benign method was developed for the synthesis of various N-aryl and N-alkyl sulfonamides in water. Trichloroisocyanuric acid (TCCA) was used for the oxidative chlorination of disulfides and thiols to produce the corresponding sulfonyl chloride, which reacted in situ with different amines in the absence of organic bases, to furnish sulfonamides in good to excellent yields. The isolation of the products involves simple experimental conditions and a product isolation procedure (only filtration) in the absence of organic solvents, which makes this protocol potentially useful in the development of a green strategy for the synthesis of sulfonamides.
A Novel Approach to the Practical Synthesis of Sulfides
We have demonstrated a facile and direct synthesis of sulfide derivatives using acetals and ketals, derived from aromatic/ conjugated aldehydes and aromatic ketones, with disulfides and the InBr 3 -Et 3 SiH reducing system. We also succeeded [a] 4123 in developing an unprecedented one-pot preparation of an aliphatic sulfide from a disulfide and an aliphatic acetal. (