Über 1.4‐Amino‐thiophenol. II

Abstract

Ebenso bietet die Diazotierung des A m i n o s u l f i d s (I.) keirle Schwierigkeiten; das D i a z o n i u n i s a l z ist sehr reaktionsfahhig, es kann in bekannter Weise in das J o d i d (VII.) und in das C y a n i d (VIII.) ubergefiihrt werden, aus welch' letzterem d a m die Siiure (IX.) dargestellt wurde. J CN COOH VIII. q ; IX. I'] \/ \ / VII. ('1 \/ S. CHs S . CHa s .CN3 1) Ente Mitteilnng: Dieso Berirhte 43, 3362 [1909]. Auch die n i a z o a m i d o v e r b i n d u n g ist leicht zugiinglich; wenig glatt verliiuft dagegen die Reaktion beim Verkochen des Diazoniumsalzes. (Vergl. den esperimentellen Teil.) Naher untersucht haben wir die J o d v e r b i n d u n g (VII.); sie addiert leicht Brom unter Bildung eines D i b r o m i d s (X.), melches durch Wasser in dns S u l f o x y d ( X I ) ilbergeht. Dasselbe S u l f o x p d entsteht bei der Orydation des Jodida mit Salpetersiiure; durch Broinwasserstolf wird es in dns D i b r o m i d (X.) umgewandelt. J C12 I\ / l .

Cleavage of the Carbon-Sulfur Bond in Divalent Sulfur Compounds.

“…The action of halogens, and chlorine in particular, on compounds of the type ArSCH3 (cf. page 37) has been studied; the first product of chlorination is usually the -SCCI3 derivative (453,455) and this can be converted to the thiophenol in several ways. In the presence of water, the sulfonyl chloride may be obtained (458).…”

Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

“…Chemical treatment of N‐(3,4‐dioxo‐3,4‐dihydronaphthalen‐1‐yl)cyanamide ( 28 ) with HCl or H 2 SO 4 yielded 1 . Therefore, heating of 4‐(phenylamino)naphthalen‐1,2‐dione ( 29 ) in HCl, H 2 SO 4 , or acetic acid produced 1 . Treatment of 4‐aminonaphthalen‐1,2‐dione ( 30 ) in alkaline solution gave 1 .…”

“…Then, hydrolysis followed by decarboxylation of ethyl 3‐hydroxy‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐carboxylate ( 52 ) gave 1 . The reaction of 2‐(phenylamino)‐2,3‐dihydronaphthalen‐1,4‐dione ( 53 ) with H 2 SO 4 in EtOH , or with NaOH yielded 1 . Finally, the oxidation of 2‐allylnaphthalen‐1,4‐dione ( 54 ) with H 2 O 2 in aqueous KOH gave compound 1 (Scheme ).…”

Distinct fragmentation patterns of the radical anions derived from 1-halo-2- and -4-(phenylmethylthio)benzenes

“…This compound was isolated and purified (on silica gel, eluted with petroleum ether-diethyl ether (98 : 2)) from the photoreaction mixture, and characterised by spectroscopic data, which match those reported in the literature. 23 GC-MS EI, m/z 200 (M ϩ. , 100%), 184 (95), 185 (100), 165 (10), 152 (43), 139 (15), 115 (2), 89 (1), 77 (4), 63 (5), 51 (13), 39 (17), 32 (23).…”