Phase transfer catalyzed desulfurization reactions

✍ Scribed by Howard Alper; Fazle Sibtain; Josef Heveling

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 162 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87860-0

✦ Synopsis

Mercaptans react with triiron dodecacarbonyl or dicobalt octacarbonyl, under phase transfer catalysis conditions, to give hydrocarbons in good yields. Phase transfer catalysis ls2 is a valuable method for effecting a variety of reactions involving organometallic compounds as stoichiometric reagents or catalysts3. Examples include the dicobalt octacarbonyl induced carbonylation of Schiff bases to ally1 amides,4 the palladium(o) catalyzed conversion of vinylic dibromides to monoacids or diacids,S, and the ruthenium(II) catalyzed reduction of nitrocompounds by synthesis gas6. We now wish to report the first examples of desulfurization reactions effected by phase transfer catalysis. Treatment of o-methylbenzyl mercaptan [~,R,=o-CH,C,H,,R,=R,=H] with triiron dodecacarbonyl in benzene, sodium hydroxide as the aqueous phase, and tetra-n-butylammonium hydrogen sulfate as 5N NaOH,C,H, R1R2R3CSH + Fe3(C0)12