6251-33-8

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 6251-34-9 1-thiacycloheptane 1-oxide 
• 4753-80-4 thiepane 
• 2695-47-8 6-Bromo-1-hexene 
• 133216-86-1 hex-5-ene-1-sulfonyl chloride 

Downstream Products

• 423-50-7 tridecafluorohexanesulfonyl fluoride 

Relevant academic research and scientific papers

A kinetic investigation, supported by theoretical calculations, of steric and ring strain effects on the oxidation of sulfides and sulfoxides by dimethyldioxirane in acetone

The oxidations of alkyl 4-nitrophenyl, and dialkyl, sulfides and sulfoxides by dimethyldioxirane in acetone occur by concerted mechanisms but the sulfides respond differently from the sulfoxides to variation in the alkyl group. The reactions of the sulfides are inhibited by the steric effects of alkyl groups and these predominate over their inductive effects. By contrast, the reactions of these limited sets of sulfoxides are insensitive to alkyl steric effects but there is an indication of steric acceleration when a broader set of sulfoxides is considered. This behaviour is rationalised in terms of the differences in dipolar charge and its solvation between the ground state and transition state for the two types of substrate. The oxidations of cyclic sulfides and sulfoxides also exhibit contrasting behaviour. The reactivity of the sulfides is insensitive to ring strain but is explicable in frontier orbital terms whereas that of the sulfoxides is partly dependent upon the change in ring strain between reactant and product on oxidation, a difference rationalised in terms of the relative positions of the transition states in the reaction coordinates of the two oxidations. The reactivity of 4-, 5- and 6-membered cyclic sulfoxides is also dependent on a ring-size related property of the transition state. Calculations at the B3-LYP/6-31G* level of density functional theory on both ground states and transition states, including simulation of solvation by acetone, strongly support the mechanistic conclusions reached in this and earlier work.

Mechanistic organic chemistry in a microreactor. Zeolite-controlled photooxidations of organic sulfides

The intrazeolite and solution photooxygenations of a series of sulfides have been compared. The unusual zeolite environment enhances the rates of reaction, it suppresses the Pummerer rearrangements, and it has a dramatic effect on the sulfoxide/sulfone ratio. A detailed kinetic study utilizing trapping experiments and intramolecular competition provides evidence for cation complexation to a persulfoxide intermediate as the underlying phenomenon for the unique intrazeolite behavior. For example, the enhanced rate of reaction is traced to the cation stabilization of the persulfoxide toward unproductive decomposition to substrate and triplet oxygen.

Sulphonate Esters as Sources of Sulphonyl Radicals; Ring-closure Reactions of Alk-4- and -5-enesulphonyl Radicals

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.

Regioselectivity in the formation of cyclic sulphones from 4- and 5-alkenesulphonyl chlorides

Alk-4-enesulphonyl chlorides and alk-5-enesulphonyl chlorides cyclise under free radical conditions mainly in the endo mode to give tetrahydrothiopyran-1,1-dioxide and thiepane-1,1-dioxide respectively.

PHOTOSENSITIZED OXYGENATION OF CYCLIC SULFIDES. SELECTIVE C-S BOND CLEAVAGE

TPP-Senzitized photooxidation of five-membered ring sulfides in aprotic solvent afforded C-S bond cleavage products, unlike six- and seven-membered ring sulfides which gave only S-oxidation products.The products as well as substitution and concentration effects suggest that C-S bond cleavage depends upon acidity of α-proton of persulfoxide intermediate.

Cathodic Reduction of SO2 in the Presence of Organic Dihalides

The reaction of the electrolytically generated SO2 anion radical with 1,ω-dihalides is used for the synthesis of sulfur containing heterocycles like oxathiolane-, oxathiane-, thiane- and thiepane-oxides. 1,2-Dihalides are reductively deblocked to give olefines. - Keywords: Sulfur dioxide reduction; Sulfones; Sulfinic esters, cyclic

Sulfur Heterocycles. 3. Heterogeneous, Phase-Transfer, and Acid-Catalyzed Potassium Permanganate Oxidation of Sulfides to Sulfones and a Survey of their Carbon-13 Nuclear Magnetic Resonance Spectra

Although numerous oxidation methods are available for the transformation of sulfides into sulfones, low-molecular-weight, heterocyclic sulfides are often not amenable to this oxidation techniques.The method presented here is a general and economical oxidation using potassium permanganate and various catalysts.Nineteen low-molecular-weight and heterocyclic sulfides were successfully oxidized by variations of this technique, and the results are presented here.In addition, the carbon-13 NMR spectra of these compounds and about two dozen others are reported.General chemical shift trends are reported for selected compounds, and details can be found in the supplementary material.