A Synthesis of Formamidinesulfinic Acids and Formamidines

N,N'-dimethylthiourea dioxide formation from N,N'-dimethylthiourea reflects hydrogen peroxide concentrations in simple biological systems.

“…Reaction of Me2TU and H202 yielded a single peak on HPLC (Fig. 1) or GC (data not shown) tracings (28,29). Elemental analyses revealed that the product from reaction of Me2TU with H202 fit the predicted formula C3H8N202S for Me2TU dioxide.…”

Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols

“…These findings suggest that RFT can promote the photodecomposition of thiourea by two pathways,b ym eans of singlet O 2 and byproduct H 2 O 2 . [23] In the reaction with 1b,i ti sl ikely that the singlet O 2 pathway is predominant because the formation of H 2 O 2 needs at least one turnover of the flavin catalyst and is thus slow,given the small amount of product generated.…”

Recent Developments in the Chemistry of Thiourea Oxides

“…All of them are significantly less stable in alkaline solutions than in neutral or acidic conditions. On heating in glacial acetic acid, TDO decomposes to give formamidine acetate and sulfur dioxide 24. The corresponding ureas are the only nitrogen‐containing products of thiourea, N ‐methylthiourea, and N,N′ ‐dimethylthiourea dioxides in strongly alkaline solutions 50.…”

“…[18] For many years TDO remained the only known oxide of thioureas, until Bçeseken [19] and later Walter and coworkers [20] published a series of papers on the synthesis of the dioxides and trioxides of thioureas in aqueous solutions. The synthesis of dioxides and trioxides was also carried out by Yarovenko and Lastovskii; [21] Miller, Bischoff and Pae; [22] De Filippo and co-workers; [23] Havel and Kluttz; [24] Kim and co-workers; [25] and Maryanoff and co-workers. [26] It should be noted that the most convenient oxidant to prepare thiourea trioxide (TTO) is peracetic acid.…”

“…On heating in glacial acetic acid, TDO decomposes to give formamidine acetate and sulfur dioxide. [24] The corresponding ureas are the only nitrogen-containing products of thiourea, N-methylthiourea, and N,N'-dimethylthiourea dioxides in strongly alkaline solutions. [50] In less alkaline media (pH 10) cyanamides as well as ammonia are also formed [22b] (ammonia is formed when thiourea trioxide decomposes in weakly acidic media, [28] as well).…”