Herstellung von Arenthiosulfonsäure-S-arylestern durch Thermolyse von Arensulfonsäure-hydraziden

Thiosulfonates as Emerging Reactants: Synthesis and Applications

“…Over the years various promoting agents have been reported to achieve the selective oxidation of one sulfur atom in disulfides ( 3 ) (Scheme ). Peracids like m ‐chloroperoxybenzoic acid ( m ‐CPBA, route 1) or hydrogen peroxide (H 2 O 2 ) in acetic acid (route 2) are the most common oxidizing agents used for this purpose. Espenson and co‐workers reported the use of hydrogen peroxide as stoichiometric oxidant in the presence of methyltrioxorhenium (CH 3 ReO 3 =MTO) as catalyst (route 3) .…”

“…Sulfonyl hydrazides ( 12 ) are easily accessible and stable solids, which have also been studied for the preparation of symmetrical thiosulfonates ( 7 ). The first report was presented in 1972 by Meier and Menzel, who discovered the thermal decomposition of arenesulfonyl hydrazides ( 12 ), with N 2 evolution, upon heating above their melting point (Scheme , route 1) . The absence of solvent gives a very low PMI, although calorimetric data are required to evaluate the safety of this method for use at scale.…”

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

“…On the basis of previous reports and the results of the control experiments, [11][12][13][14]16 we try to postulate a probable mechanism as shown in Scheme 4. Initially, intermediate A was generated by the reaction of 4-methylbenzenesulfonohydrazide (1a) with NaHSO 2 •CH 2 O.…”

“…10 In 1972, Meier and coworkers first reported the preparation of thiosulfonates via thermal decomposition of arenesulfonyl hydrazides, upon heating above their melting point (Scheme 1a). 11 Guo utilized a catalytic system based on Pd/ZrO 2 nanocomposite photocatalyst to obtain thiosulfonates in moderate to good yield (Scheme 1b). 12 Another approach discovered by the group of Wei delivers thiosulfonates in high yields in the presence of NIS/K 2 S 2 O 8 /THF at 70 °C (Scheme 1c).…”

An Alternative Method for the Synthesis of S-Methylmethanethiosulfonate

“…In general, thiosulfonic S-esters are stable and reactive species; however their use has been limited by the lack of easy and practical preparations. A number of methods are known for the preparation of S-Methylmethanethiosulfonate which involves harmful toxic reagents or typical lengthy work-up which distract the interest of chemists [16][17][18][19][20][21][22][23][24]. Herein, we report a novel and very simple method for the synthesis of the title compound.…”