RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2012; 23(13): 1893-1896
DOI: 10.1055/s-0032-1316557
DOI: 10.1055/s-0032-1316557
letter
Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions
Weitere Informationen
Publikationsverlauf
Received: 07. Mai 2012
Accepted: 24. Mai 2012
Publikationsdatum:
23. Juli 2012 (online)
![](https://www.thieme-connect.de/media/synlett/201213/lookinside/thumbnails/10.1055-s-0032-1316557-1.jpg)
This paper is dedicated to Professor Rudolf Leuckart for his studies on mercaptans.
Abstract
In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines.
-
References
- 1 Fan X, He Y, Wang Y, Xue Z, Zhang X, Wang J. Tetrahedron Lett. 2011; 52: 899
- 2 Ławecka J, Olender E, Piszcz P, Rykowski A. Tetrahedron Lett. 2008; 49: 723
- 3 Remacle F, Kryachko ES. Mol. Struct. 2004; 708: 165
- 4 Blower PJ, Dilworth JR. Coord. Chem. Rev. 1987; 76: 121
- 5 Fleischer H. Coord. Chem. Rev. 2005; 249: 799
- 6 Milnes JT, Witchel HJ, Leaney JL, Leishman DJ, Hancox JC. Biochem. Biophys. Res. Commun. 2006; 351: 273
- 7 Rotstein DM, Walker KA. M. Tetrahedron: Asymmetry 1993; 4: 1521
- 8 Remuzzi G, Lesti M, Gotti E, Ganeva M, Dimitrov BD, Ene-Iordache B, Gherardi G, Donati D, Salvadori M, Sandrini S, Valente U, Segoloni G, Mourad G, Federico S, Rigotti P, Sparacino V, Bosmans J.-L, Perico N, Ruggenenti P. Lancet 2004; 364: 503
- 9 Sacko M, De Clercq D, Behnke JM, Gilbert FS, Dorny P, Vercruysse J. Trans. R. Soc. Trop. Med. Hyg. 1999; 93: 195
- 10 O’Connor GB. Am. J. Surg. 1939; 45: 563
- 11 Desiato MT, Palmieri MG, Giacomini P, Scalise A, Arciprete F, Caramia MD. J. Neurol. Sci. 1999; 169: 98
- 12 Bahrami K, Khodaei MM, Abbasi J. Tetrahedron 2012; 68: 5095
- 13a Sambasivam S, Joseph DP, Reddy DR, Reddy BK, Jayasankar CK. Mater. Sci. Eng., B 2008; 150: 125
- 13b Pattabi M, Amma BS. Sol. Energy Mater. Sol. Cells 2006; 90: 2377
- 14a Azizian-Kalandaragh Y, Khodayari A, Behboudnia M. Mater. Sci. Semicond. Process. 2009; 12: 142
- 14b Kamat PV In Studies in Surface Science and Catalysis. Vol. 103. Meisel D. Elsevier,; 1997: 237
- 15 Schneider P. US 2784167, 1957
- 16 Leuckart R. J. Prakt. Chem. 1890; 41: 179
- 17 Cox JR. Jr, Gladys CL, Field L, Pearson D. J. Org. Chem. 1960; 25: 1083
- 18 Tournier L, Zard SZ. Tetrahedron Lett. 2005; 46: 971
- 19 Li JJ. Name Reactions: Newman–Kwart Rearrangement. 3rd ed., Vol. 34, 2009;
- 20 Moseley JD, Sankey RF, Tang ON, Gilday JP. Tetrahedron 2006; 62: 4685
- 21 Flores-Figueroa A, Arista MV, Talancón-Sánchez D, Castillo I. J. Braz. Chem. Soc. 2005; 16: 397
- 22 Levy J, Paramus N, Psihas J. US 3326981, 1967
- 23 Bellale EV, Chaudhari MK, Akamanchi KG. Synthesis 2009; 3211
- 24 Crenshaw RR. US 3413305, 1968
- 25 Jiang Y, Qin Y, Xie S, Zhang X, Dong J, Ma D. Org. Lett. 2009; 11: 5250
- 26 Bräse S, Banert K. Organic Azides: Syntheses and Applications . Wiley; Chichester: 2009
- 27a Rakotondradany F, Williams CI, Whitehead MA, Jean-Claude BJ. J. Mol. Struct. (Theochem) 2001; 535: 217
- 27b Pages T, Langlois BR. Fluorine Chem. 2001; 107: 321
- 27c Picherit C, Wagner F, Uguen D. Tetrahedron Lett. 2004; 45: 2579
- 28a Reingruber R, Vanderheiden S, Muller T, Nieger M, Es-Sayed M, Bräse S. Tetrahedron Lett. 2009; 50: 3439
- 28b Lazny R, Poplawski J, Kobberling J, Enders D, Bräse S. Synlett 1999; 1304
- 28c Arseniyadis S, Wagner A, Mioskowski C. Tetrahedron Lett. 2002; 43: 9717
- 29 Hansen MN, Farjami E, Kristiansen M, Clima L, Pedersen SU, Daasbjerg K, Ferapontova EE, Gothelf KV. Org. Chem. 2010; 75: 2474
- 30 Harmata M, Hong X, Zheng P. Tetrahedron Lett. 2006; 47: 7343
- 31 Pool B. J. Cancer Res. Clin. Oncol. 1979; 93: 221
- 32 Kawanisi M, Ôtani I, Nozaki H. Tetrahedron Lett. 1968; 9: 5575
- 33a Shirini F, Zolfigol MA, Khaleghi M. Mendeleev Commun. 2004; 14: 34
-
33b Zolfigol MA. Tetrahedron 2001; 57: 9509
- 34 Yu BC, Shirai Y, Tour JM. Tetrahedron 2006; 62: 10303