Studies of Organosulfur Compounds. VI. The Preparation of Carbamoyl Esters of Aromatic Dithio Acids and Their Spectral Properties

Abstract

It was found that aromatic dithio acids readily reacted with aryl isocyanate at room temperature to give the corresponding mixed thioanhydrides with the general formula of (ArCS·S·CONHAr) in excellent yields as stable crystals. The mixed thioanhydrides reacted with primary amines at room temperature to give the corresponding thioamides and asymmetric ureas, while the reaction with secondary amines gave the corresponging amine salts and asymmetric ureas in good yields. The spectral properties of the mixed thioanhydrides were discussed.

Thion (RCSOH), Selenon (RCSeOH), and Telluron (RCTeOH) Acids as Predominant Species

“…We previously found that dithiocarboxylic acids reacted with aryl isocyanates to give thioacyl carbamoyl sulfides (RCS−S−CONHR‘, R, R‘ = alkyl, aryl) in good yields, and in which the existence of hydrogen bonding between the NH hydrogen and thiocarbonyl sulfur atoms was suggested by infrared study …”

Acyl carbamoyl selenides and related sulfur isologues: synthesis and x‐ray structural analyses

“…Previously, we reported that the NH proton chemical shifts in thioacyl carbamoyl sulfides (I, E ‫ס‬ EЈ ‫ס‬ S) appeared at unusually low fields, below d 12, indicating the presence of an intramolecular C‫ס‬S • • • HN hydrogen bond [3]. As shown in Table 1 …”

“…Previously, we reported the isolation of a series of dithiocarboxylic carbamic mixed acid anhydrides I (E ‫ס‬ EЈ ‫ס‬ S) as crystals by reacting dithiocarboxylic acids with aryl isocyanates [3]. Since then, several carbamic thiocarboxylic mixed acid anhydrides I (E ‫ס‬ O, EЈ ‫ס‬ S) have been reported by Motoki et al [4].…”

Hydrogen bonding in 2-hydroxybenzoyl and 2-hydroxythiobenzoyl compounds: Spectroscopic characterization and spectroscopic bond strength sequences

“…For convenience the compounds are divided into 6 groups: (I) acid chlorides (1); (II) tertiary amides (2-4); (III) acids and esters (5)(6)(7)(8); (IV) aldehydes and ketones (9)(10); (V) primary and secondary amides (11-13); (VI) salts (14-17). For the preparation and characterization of the majority of the compounds see the references given in Table 1 S-Methyl-2-hydroxy-thiobenzoate (O8), CsHsO2S, was prepared from 2',6'-dimethylpiperidinium-2-hydroxy-thiobenzoate and methyl iodide [21] and purified by liquid chromatography (CHCI a:nheptane = 1:4): yellow oil; 1H NMR (CCI4:CDC13 …”