Catalyst-Free Efficient Regioselective Ring Opening of Oxiranes with Thioacids in Water

Novel triethylamine catalyzed S → O acetyl migration reaction to generate candidate thiols for construction of topological and functional sulfur-containing polymers

“…19 The subsequent intramolecular SOAM in a TEA-solvent mixture (volume ratio: 1/5-1/1) at a concentration of 0.1 mol L À1 could rapidly transform 2 into b-acetate thiols 3 via an intramolecular mode. Thus, a toolbox of various candidate thiols is presented to the polymer science community for future use.…”

“…The reaction could take place in water or by using catalytic amount of TEA (1.0 mol%). 19 The subsequent intramolecular SOAM in a TEA-solvent mixture (volume ratio: 1/5-1/1) at a concentration of 0.1 mol L À1 could rapidly transform 2 into b-acetate thiols 3 via an intramolecular mode. b-Hydroxy thiols 4 and diacetates 5 were also isolated, indicating that a simultaneous intermolecular migration reaction also took place.…”

Epihalohydrins in Organic Synthesis

“…Furthermore, the ring opening of epichlorohydrin ( 5 ) with 4-fluorobenzene sulfinic acid ( 29 ) has been carried out to form 3-(4-fluorophenylsulfonyl)prop-2-ene-1-ol ( 30 ) by subsequent nucleophilic substitution and eliminative ring opening (Scheme ) . A catalyst-free efficient regioselective ring opening of epichlorohydrin ( 5 ) and epibromohydrin ( 6 ) has been accomplished by thiobenzoic acid in water to form the corresponding 3-halo-2-hydroxypropylbenzothioates in quantitative yields …”

“…89 A catalyst-free efficient regioselective ring opening of epichlorohydrin ( 5) and epibromohydrin (6) has been accomplished by thiobenzoic acid in water to form the corresponding 3-halo-2-hydroxypropylbenzothioates in quantitative yields. 90 On the basis of the same methodology, the selenolysis of epichlorohydrin ( 5) with aryl selenols using the ionic liquid [Bmim]BF 4 as a catalyst has been demonstrated to form βhydroxyselenides in excellent yields. 83 Some other methods for the synthesis of β-hydroxyselenides involve the reaction of epichlorohydrin (5) with benzeneselenol in water under supramolecular catalysis in the presence of β-cyclodextrin 91 or in dichloromethane using ammonium 12-molybdophosphate (Scheme 13), 92 and with diselenides mediated by Zn/AlCl 3 .…”

[Fe3O4@SiO2@(CH2)3im]C6F5O as a New Hydrophilic and Task‐Specific Nanomagnetic Catalyst: Application for Synthesis of β‐Azido Alcohols and Thiiranes under Mild and Green Conditions

“…Because of high angle strain, their ring can be opened by various nucleophilic reagents and several 1,2‐disubstitued molecules will be produced. Phthalimide, indoles, phenols, thiols,, thiophenols,,, benzotriazole, alcohols,, acetic acid, H 2 O, azide, sulfide, cyanide and acid chlorides are examples of nucleophiles that have be used for this purpose. Some cyclic carbonate and sulfites were synthesized by silica‐immobilized homogeneous catalysts.…”