Ueber Bildung von Anhydroverbindungen des Orthoamidophenylmercaptans aus Thioaniliden

Abstract

HsO 18.94 19.09 pct. Kupferbestimmung (im wasserfieien Salz): 0.1968 g Substanz ergabeu 0.051 g Kupferoxyd, entsprechend 0.0406 g Eupfer. Gefunden Ber. fiir CI SHl e : : 2 >* Cu Cu 20.63 20.65 pCt. S 0 s Ag T h i o p h e n d i s u l f 0% a u r e s S i 1 b e r , Cq SH:, *:: s o3 I n gleicher Weise wurde durch Absattigen der freien Disulfosliure Es krystallisirt aue der I n Das Salz enthlilt kein mit Silbercarbonat das Silbersalz erhalten. Losung in kleinen, biischelformig zu Warzen vereinigten Nadeln. warmem Wasser ist es zienilich leicht liislich. Krystallwasser. Die Silberbestimmung ergab: Fiir 0.1909 g Substanz 0.0894 g Silber. Gefunden Ber. fiir Cd SH1-:: O3 * *g SOa. A g Ag 46.83 47.16 pCt. Z i i r i c h , Chem.-analyt. Laboratorium des Polytechnikums. 227. P. Jacobson: Ueber Bildung von Anhydroverbindungen des 01.thoemidophenylmercaptans Bus Thioaniliden. (Vorgetragen in der Sitzung vom Verfasser.) Die im Folgenden beschriebenen Versuche, welche Umwandlungen von T h i o a n i l i d e n , R. CSNH. CgH5, in A n h y d r o d e r i v a t e d e s A m i d o p h e n y l m e r c a p t a n s : kennen lehren, wurden veranlasst durch einige, in einem anderen Gebiete gesammelte Beobachtungen, die hier zunachst kurz erwlihnt werden mijgen.

On the Origin of Higher Rotational Barriers in Thioamides than in Amides. Remote Substituent Effects on the Conformational Stability of the Thioamide Group in Thioacetanilides

“…The p -substituted thioacetanilides were prepared by treatment of the respective anilides with phosphorus pentasulfide in boiling solvents (pyridine, toluene). , The IR spectra of the compounds were obtained in chloroform solutions on a Perkin−Elmer model 983G spectrometer. The N−H stretching mode frequencies were measured with an accuracy of ±1 cm -1 .…”

Iron‐Catalyzed Regioselective Synthesis of 2‐Arylbenzoxazoles and 2‐Arylbenzothiazoles via Alternative Reaction Pathways

“…Based on the iron(III)‐catalyzed activation of NBS, a mechanism for benzothiazole formation was proposed (Scheme a). In a similar fashion to the preparation of benzothiazoles by S ‐cyclization of N ‐arylthiobenzamides using the Jacobson method involving potassium ferricyanide and the Hugerschoff reaction with bromine, we propose that the iron(III) complexed NBS species results in activation of the sulfur atom, yielding S ‐bromide intermediate 5 . Following formation of 5 , the transformation is completed by an intramolecular electrophilic aromatic substitution step.…”

In vivo photocontrol of microtubule dynamics and integrity, migration and mitosis, by the potent GFP-imaging-compatible photoswitchable reagents SBTubA4P and SBTub2M

“…We first tested whether restoring the methoxy groups of the CA4 pharmacophore would increase potency despite the extra size, with SBTubA4 (1). This, like most SBTubs, was synthesised in a short sequence (Fig 1e) via basic aldol condensation of the derivatised 2-methylbenzothiazole with the corresponding benzaldehyde, with the 2-methylbenzothiazole obtained via Jacobson cyclization 31 of the thioacetanilide using potassium ferricyanide (exceptions were para-aniline 7 which was obtained by Horner-Wadsworth-Emmons olefination; and 9 and 11 where the 2,5-and 2,7-dimethylbenzothiazoles were synthesised by Ullmann-type coupling according to Ma 32 since Jacobson cyclization of 3-methyl-thioacetoanilide gave an inseparable mixture; see Suppporting Information for details). SBTub3 complex (carbons as purple spheres).…”