38045-54-4Relevant academic research and scientific papers
CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates
Kim, Junsu,Park, Sanggil,Kim, Hyungjun,Kim, Jinho
supporting information, (2020/07/02)
Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.
Synthesis of N-substituted derivatives of arylsulfonyl hydrazides and their investigation as additives for lubricating oils
Mamedov,Mamedova,Guseinov,Ladokhina,Fatalizade,Farzaliev
, p. 284 - 287 (2012/10/29)
The reaction between arylsulfonyl chlorides and hydrazine has been studied, and it has been found that in the presence of excess hydrazine, the bis-derivatives are produced in small amounts along with monoarylsulfonyl hydrazides. It has been revealed that the reaction of monosulfonyl hydrazides with alkyl bromides in the presence of a base results only in N-alkylation of the sulfamide nitrogen, although the reaction in the presence of HCl proceeds at the amine group with the formation of quaternary ammonium salts. A method for the preparation of sulfonyl hydrazides by oxidation of N-alkyl sulfamides in the presence of iodine has been developed. Some arylsulfonyl hydrazide derivatives have been examined as antioxidant, anti-rust, and antiwear additives. These sulfonyl hydrazides also exhibit a high bactericidal and fungicidal activity.
