25195-63-5Relevant academic research and scientific papers
Sodium Dithionite-Mediated Decarboxylative Sulfonylation: Facile Access to Tertiary Sulfones
Chen, Shihao,Jiang, Xuefeng,Li, Yaping,Wang, Ming
, p. 8907 - 8911 (2020/04/22)
A straightforward multicomponent decarboxylative cross coupling of redox-active esters (N-hydroxyphthalimide ester), sodium dithionite, and electrophiles was established to construct sterically bulky sulfones. The inorganic salt sodium dithionite not only served as the sulfur dioxide source, but also acted as an efficient radical initiator for the decarboxylation. Notably, diverse naturally abundant carboxylic acids and artificially prepared carboxyl-containing drugs with multiple heteroatoms and sensitive functional groups successfully underwent this decarboxylative sulfonylation to provide sterically bulky tertiary sulfones. Mechanistic studies further demonstrated that decarboxylation was the rate-determining step and occurred via a single-electron transfer (SET) process with the assistance of sodium dithionite.
Large-steric-hindrance alkyl-alkyl sulfone compound as well as synthesis method and application thereof
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Paragraph 0169-0172, (2020/07/24)
The invention belongs to the technical field of organic compound synthesis and application, and discloses a large-steric-hindrance alkyl-alkyl sulfone compound shown as a formula (4) and a synthesis method thereof. Carboxylic acid derived redox ester, a reducing sulfur dioxide source and an alkyl electrophilic reagent are used as raw materials, and a series of large-steric-hindrance alkyl-alkyl sulfone compounds are obtained by a three-component one-pot method. The synthesis method is wide in raw material source, cheap and easy to obtain; the reaction operation is simple; the functional grouptolerance is high; the use of a reducing sulfur dioxide source in the reaction avoids the addition of an additional equivalent metal reducing reagent, is economical and practical, and avoids the pollution of waste metals to the environment. The invention also discloses application of the alkyl-alkyl sulfone compound in preparation of drugs, pesticides, organic photoelectric materials and the like.The method has high practical value and wide application prospect.
Nucleofugality of the Sulfinate Group in Carbocation-Forming Processes
Creary, Xavier
, p. 5080 - 5084 (2007/10/02)
The solvolytic reactivity of a variety of sulfones and sulfinate esters has been determined which allows one to place the sulfinate leaving group in a relative nucleofugality scale.Cumyl trifluoromethyl sulfone (1) reacts in a variety of solvents to give substitution products.The mOTs value of 0.82 is indicative of the involvement of the cumyl cation (9) formed in kc process.In terms of rate, 1 is 170 times less reactive than cumyl chloride but 286 times more reactive than cumyl p-nitrobenzoate.The analogous cumyl methyl sulfone (2) and cumyl phenyl sulfone (3) solvolyze approximately 107 times more slowly than 1.The sulfinate esters cumyl methanesulfinate (6) and cumyl p-toluenesulfinate (7) are considerably more reactive than the analogous sulfones.Methanolysis of 6 was also subject to acid catalysis, where a mechanism analogous to the AAL1 mechanism of hydrolysis of esters of carboxylic acids was suggested.The less hindered α-phenethyl trifluoromethyl sulfone (4) and p-methoxybenzyl trifluoromethyl sulfone (5) solvolyzed at rates that approached those of the analogous p-nitrobenzoates.This was indicative of the importance of relief of steric congestion in solvolyses of the more hindered tertiary sulfone 1.
