53657-58-2

Upstream product

• 110-83-8 cyclohexene 
• 931-59-9 benzenesulfenyl chloride 
• 4837-31-4 4-Phenylsulfanyl-morpholine 
• 107-19-7 propargyl alcohol 

Downstream Products

• 110-83-8 cyclohexene 

Relevant academic research and scientific papers

Iodosulfenylation of olefins with sulfenamides in the presence of metal iodides

Reactions of arylsulfenamides, arylsulfenates, thiobisamines, and dithiobisamines with olefins in the presence of zinc, tin(II), tin(IV), antimony(III), or magnesium iodides were investigated. In the case of cage olefins, the reactions afford mixtures of 1,2-iodosulfides and diiodides, the ratio between which depends on the type of iodine-containing Lewis acid. Iodosulfides were obtained in the highest yields in the reactions of cage olefins upon activation with zinc or tin(II) iodides. In the case of olefins prone to the Wagner - Meerwein rearrangement (bicyclo[2.2.1]heptanes) or to the addition - elimination reaction (camphene), the corresponding products formed. A reaction mechanism is proposed.

Linear Paired Electrolysis—Realising 200 % Current Efficiency for Stoichiometric Transformations—The Electrochemical Bromination of Alkenes

The generation of bromine by oxidation of bromide anions at the anode and reduction of molecular oxygen at the cathode to hydrogen peroxide resulted in the overall formation of two molecules of Br2 (=four electron oxidation) by passing just two electrons through the solution. The bromine was used for the bromination of alkenes and thereby a linear paired electrolysis was attained which resulted in current efficencies of up to 200 %. Also, the diiodination of cyclohexene as well as the electrophilic aromatic bromination of an electron-rich arene were realised both in 168 % current efficiencies.

I-/IO3- assemblies as promoters of iodohydrin formation

The direct conversion of olefins to their corresponding iodohydrins is efficient with I-/IO3- assemblies in an aqueous acidic medium. Iodohydrins were obtained in moderately good yields at ambient reaction conditions without employing any metal catalysts.

Reductive free-radical alkylations and cyclisations mediated by 1-alkylcyclohexa-2,5-diene-1-carboxylic acids

A range of 1-alkylcyclohexa-2,5-diene-1-carboxylic acids were prepared by Birch reduction-alkylation of benzoic acid and their efficiency as mediators of alkyl radical chain addition and cyclisation processes was investigated. Reductive alkylations were respectably successful, even with only one or two equivalents of alkene, for secondary, tertiary and benzylic radicals. Reaction of 1-[2-(cyclohex-2-enyloxy)ethyl]cyclohexa-2,5-diene-1-carboxylic acid yielded the product of exo-trig-cyclisation, i.e. 7-oxabicyclo[4.3.0]nonane, in a yield comparable to that obtained from the tributyltin hydride induced cyclisation of 3-(2′-iodoethoxy)-cyclohexene. This, together with the isolation of both exo- and endo-cyclisation products from 1-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethoxy)ethyl]cyclohexa-2,5-diene- 1-carboxylic acid established that ring closures could also be satisfactorily mediated with these reagents. Preparations were completely free of metal contaminants and direct reduction of the alkyl radicals, prior to addition or cyclisation, was completely absent. However, the desired products were accompanied by alkylbenzenes, together with by-products from the initiator decompositions, and this complicated work-up. Failure to obtain 1-[2-(prop-2-yn-1-yloxy)cyclohexyl]cyclohexa-2,5-diene-1-carboxylic acid in Birch reductive alkylations with trans-1-iodo-2-(prop-2-yn-1-yloxy)cyclohexane (and the corresponding bromide) indicated a limitation on precursor synthesis. The Birch reduction-alkylation was not of universal applicability and was suppressed for alkyl halides having β-substituents.

An Efficient Method for the Copper(II)-promoted Stereoselective Iodofunctionalization of Alkenes

A mixture of iodine and CuO*HBF4 reacts stereoselectively with alkenes in the presence of a wide variety of nucleophiles (water, MeOH, HCO2H, AcOH, EtCOOH, NaNO2, KSCN, NaSO2Ar, LiCl, LiBr, NaI, Et3SiH, and MeOPh) to give the corresponding 2-functionalized iodo compounds.A regio chemistry study is also reported.

A General and Useful Copper(II)-promoted Iodofunctionalization of Unsaturated Systems

A mixture of iodine and CuO*HBF4 reacts stereospecifically with olefins in the presence of a wide variety of nucleophiles (NaNO2, NaSO2Ar, NaI, Et3SiH, MeOPh and H2O) to give the corresponding 2-functionalized iodo compounds; the same reagents also cause iodofunctionalization of 1,3-dienes and acetylenes.

The Synthesis and Some Reactions of Thiazolidine-2-selones

As a route to thiazolidine-2-selones or the tautomeric 2-thiazolines, the reactions of trans-1-iodo-2-isothiocyanatocyclohexane with selenium nucleophiles have been investigated.Sodium hydrogenselenide gives a mixture of the 2-selone (2) and 2-thione (3) while lithium selenide gives mainly the 2-thione (3).With these reagents trans-1-iodo-2-isocyanatocyclohexane gives the corresponding selenazolidin-2-one (5).Treatment of 2-lithiobenzothiazole with N-phenylselenophthalimide or diphenyl diselenide gives 2-phenylselenobenzothiazole, while reaction of the sodium salt of selenobenzothiazole with alkyl or allyl halides affords high yields of 2-alkylseleno- and 2-allylselenobenzothiazoles, respectively.Treatment of 2-decylselenobenzothiazole with either hydrogen peroxide or m-chloroperbenzoic acid leads to low yields of the Pummerer rearrangement product (40). 2-Prop-2'-enylselenobenzothiazole can be used as a transfer reagent in palladium-catalysed allylation of diethyl malonate.Alternative routes to vic-iodoselenocyanates have been investigated.

vic-Iodothiocyanates and Iodoisothiocyanates. Part 3. Further Preperations, and the Formation of 2-Alkoxy-2-thiazolines

The reactions of (E)-hex-3-ene, 4-t-butylcyclohexene, and 3-t-butylcyclohexene with iodine and potassium thiocyanate are examined.The action of iodine and thiocyanogen with (E)-hex-3-ene gives different results from those reported in the literature.Isomerization of the vic-iodothiocyatates and formation of 2-alkoxy-2-thiazolines from the latter adducts are reported.