You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via31.13.1.7 Method 7: Diazotization of Anilines Followed by Reaction with Potassium Ethyl Dithiocarbonate
Please login to access the full content or check if you have access via
Rakitin, O. A., Science of Synthesis, (2007) 31, 954.
The traditional nucleophilic aromatic substitution of arenediazonium salts by sulfur functionalities has been known since the 19th century. However, their direct conversion into thiols, by reaction with sodium sulfide, for example, has not been widely employed. A two-step procedure has made this method more widely applicable: as the sulfur nucleophile, metal thiocarboxylate[37] or, even better, potassium ethyl dithiocarbonate is used (Scheme 8).[38] The ester 16, formed via the diazo salt 15 from aniline 14, is easily hydrolyzed to give the target arenethiol 17 (Scheme 8).
Meeeee 8 Meeeeeeeeee ee 8,8,8-Meeeeeeeeeeeeeeeeeeeee eeee 8,8,8-Meeeeeeeeeeeeeeee eee eee Meeeeeeeeeeee Meeeeeeeeeeeee Meee[88]
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeeeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeeeeeeee eeeee eee eeeeeeeee eeee ee eeeeeeee eee eeeeee ee eeeeeee eeee eeee.
M eeee ee MeMM8 (8.8 e, 88.8 eeee) ee M8M (88 eM) eee eeeee eeeeeeee eeee 8 e ee e eeee ee 8,8,8-eeeeeeeeeeeeeeeee (88; 8.88 e, 88.8 eeee) ee MeMM (88 eM) eee 88% ee MMe ee 8°M. Mee eeeeeee eee eeeeeee ee 8°M eee ee eeeeeeeeee 88 eee, eee eee eeee eeeee ee e eeee ee eeeeeeeee eeeee eeeeeeeeeeeeeee (88.8 e, 888 eeee) ee M8M (88 eM) ee 88°M. Meeee eee eeeeeee eee eeeeeee eee 88 eee, ee eee eeeeee ee 88°M. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 888 eM), eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee (888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) ee eee eeeeeee eeeeeeee 88; eeeee: 8.88 e (88%). M 8 M eeeeeee eeee ee MeMM (888 eM) eee eeeee ee e eeee ee 88 (8.88 e, 88 eeee) ee MeMM (888 eM), eee eee eeeeeee eee eeeeee ee 88°M eee 8 e. Me eee eeee eeeeee ee 88°M, eeeeeeeee ee eM 8 ee eee eeeeeeee ee 88% ee MMe, eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee eeeee (888 eM), eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeee eeee 88; eeeee: 8.88 e (88%).
References
| [37] | Meeeeeee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [38] | Meeee, M.; Meeee, M. M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 88.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 88.
Return to Top