- Efficient synthesis of organic thioacetates in water
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Thioacetates as precursors of thiols are interesting starting points for synthesizing other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention that has been paid toward environmentally friendly synthetic procedures in the past decades, we prove the role and the strength of the thioacetate anion as a nucleophile for nucleophilic displacement reactions in an aqueous medium. The reactions were carried out under pH control, to prevent the decomposition of the mesylate starting materials, using potassium carbonate as a safe and mild base. A simple work up allows products to be obtained with excellent yield and acceptable purity.
- Olivito,Costanzo,Di Gioia,Nardi,Oliverio,Procopio
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supporting information
p. 7753 - 7759
(2018/11/02)
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- Sulphonate Esters as Sources of Sulphonyl Radicals; Ring-closure Reactions of Alk-4- and -5-enesulphonyl Radicals
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Alkyl alkanesulphonates and arenesulphonates were found to be useful sources of sulphonyl radicals, particularly for spectroscopic work, when treated with organotin or organosilyl radicals.Allyl, propynyl and penta-2,4-dienyl methanesulphonates gave, however, allyl, propynyl and pentadienyl radicals, respectively.Sulphonyl radicals generated in this way added efficiently to alk-1-enes with electron-releasing substituents, and the EPR spectra of the adduct radicals were recorded.A variety of radical initiation systems were tried on pent-4-enesulphonyl chloride.The pent-4-enesulphonyl radical cyclised mainly in the endo mode to give the six-membered-ring sulphone.Similarly, the hex-5-enesulphonyl radical cyclised to give thiepane 1,1-dioxide, with a seven-membered ring.The cyclohex-2-enylethanesulphonyl radical cyclised mainly in the exo mode to give 2-chloro-9-thiabicyclononane 9,9-dioxide.The mechanisms of these reactions are discussed.
- Culshaw, Peter N.,Walton, John C.
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p. 1201 - 1208
(2007/10/02)
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- GENERATION OF SULPHONYL RADICALS FROM SULPHONATE ESTERS
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Alkane alkylsulphonates and arylsulphonates are useful sources of sulphonyl radicals on treatment with organotin radicals.EPR spectra of the adduct radicals from CH3SO2* and alkenes containing donor substituents were observed.
- Culshaw, Peter N.,Walton, John C.
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p. 2457 - 2460
(2007/10/02)
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- REACTION OF PROPOSED PHOSPHOROTHIOLATE S-OXIDE INTERMEDIATES WITH ALCOHOLS
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S-Oxide 2 is an extremely reactive intermediate.Its phosphorylation vs rearrangement rates, strongly depend upon the nature of the nucleophile.
- Segall, Yoffi,Casida, John E.
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p. 209 - 212
(2007/10/02)
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