Thiocarbamates and Related Compounds. X.¹ a New Reaction of Thiocyanates

Synthesis of N‐aryl S‐alkylthiocarbamates

“…White crystals; mp 108.1-110.3 • C; IR (KBr) 1652, 3382 cm −1 ; 1 H NMR (CDCl 3 ); δ 2.96 (2H, t, J = 6.8 Hz, CH 2 ), 3.21 (2H,t,J = 7.7 Hz,CH 2 ),m,Ar),7.43 (1H,br s,NH); 13 C NMR (CDCl 3 ); δ 31. 5,36.6, 7,31.8,34.7, S-Butyl N-(4-methylphenyl)thiocarbamate 4m. White crystals; mp 73.9-75.1 • C; IR (KBr) 1651, 3297 cm −1 ; 1 H NMR (CDCl 3 ); δ 0.91 (3H, t, J = 7.6 Hz, CH 3 ), 1.40 (2H, m, J = 7.6 Hz, CH 2 ), 1.62 (2H, quint, J = 7.6 Hz, CH 2 ), 2.29 (3H, s, CH 3 ), 2.95 (2H, t, J = 7.6 Hz, CH 2 ), 7.08 (1H, d, J = 8.4 Hz, Ar), 7.23 (1H, br s, NH), 7.28 (2H, t, J = 8.4 Hz, Ar); 13 C NMR (CDCl 3 ); δ 13.…”

“…For example, S-allylic thiocarbamates were obtained from O-allylic thiocarbamates by 1,3-allyl migration from the oxygen to the sulfur atom [4]. Other routes are the reactions of alkyl thiocyanates with alcohols [5], and of amines with elemental sulfur and carbon monoxide in the presence of selenium [6]. A facile method for the preparation of thiocarbamates would certainly be very useful.…”

“…Hz, CH 3 ), 2.98 (2H, q, J = 7.2 Hz, CH 2 ), 7.09 (1H, t, J = 7.2 Hz, Ar), 7.21 (1H, br s, NH), 7.30 (2H, t, J = 7.2 Hz, Ar), 7.41 (2H, d, J = 7.2 Hz, Ar); 13 C NMR (CDCl 3 ); δ 15 5, . 24.7, 119.7, 124.4, 129.1, 137.6 (Ar), 165.8; MS (CI): m/z = 182 [M + + 1].…”

Cerium (III) Chloride as a Catalyst in the Clauson-Kaas Reaction: Synthesis and Reactivity of N-Aryl-2-thiocyanatopyrroles

“…The thiocyanate moiety can be easily transformed into other sulfur-containing functional groups, easily and conveniently leading to sulfides [18][19][20], thioesters [18], disulfides [19,20], thiols [20], thiocarbamates [21,22] and cyanothiolated compounds [23]. Interestingly enough, 2-thiocyanato-pyrrole derivatives are important intermediates in the synthesis of pyrrolo benzothiazepines, *Address correspondence of this author at the Departamento de Química, Universidade Federal de Santa Maria, UFSM, 97105-900, Santa Maria, RS, Brazil; Tel./Fax: +55-55-3220-8754; E-mail: silveira@quimica.ufsm.br which have antipsycothic activity [24,25].…”

Dreikomponentenreaktionen. I. Halogenierung von Olefinen in Gegenwart organischer Cyanverbindungen

“…Besonders intensiv ist die Protonierung (FLITTER-Reaktion) untersucht [6]. Dabei wurden auch Chlorcyan [6] und Alkylthiocyanate [7] als nucleophile Komponenten eingesetzt. Weiterhin ist die Umsetzung von Olefinen mit Quecksilber- 11-salzen [8] sowie mit Schwefeltrioxid [9] oder Chlorsulfonsaure [9 b] und Nitrilen kurz beschrieben.…”