Synthetic Routes to, Transformations of, and Rather Surprising Stabilities of (N-Methyl-N-phenylcarbamoyl)sulfenyl Chloride, ((N-Methyl-N-phenylcarbamoyl)dithio)carbonyl Chloride, and Related Compounds

• Published in: Journal of organic chemistry Vol. 76; no. 19; pp. 7882 - 7892
• Main Authors: Schrader, Alex M, Schroll, Alayne L, Barany, George
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.10.2011; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; General and physical chemistry; Kinetics and mechanisms; Organic chemistry; Photochemistry; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Physical Sciences; Reactivity and mechanisms; Science & Technology; CHEMISTRY; BIS(CHLOROCARBONYL)DISULFANE; DITHIASUCCINOYL; CONVENIENT; CARBAMOYL; DERIVATIVES; Cysteine; Phosgene; Photochemical reaction; Organic sulfide; Sulfene; Carbonyl Chlorides; Characterization; Organic disulfide; Photolysis; Reaction mechanism; Chemical synthesis; Functional group; Protecting group; Chemical transformation; Chemical reagent; Stability; Organic chlorine compounds; Sulfur containing aminoacid; Thione; Organic sulfur compounds; Protein synthesis; Carboxamide; Kinetics; Spectrophotometry; Structural analysis

The title compound classes, (carbamoyl)sulfenyl chlorides and ((carbamoyl)dithio)carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The present work reports for each of these functional groups: (i) several routes to prepare it...