Power-variable trifluoromethylating agents, (trifluoromethyl)dibenzothio- and -selenophenium salt system

✍ Scribed by Umemoto Teruo; Ishihara Sumi

• Book ID: 104226536
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 291 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)94447-2

✦ Synopsis

nor 2 reacted. 1 did not react even at lOO"C, but 1 itself decomposed. Alkaline hydrolysis of 1,3, and 4 provided interesting information regarding the trifluoromethylation mechanism. Thus, .l and 3 gave the corresponding dibenzothiophene S oxide only, while 4 gave a 1:4 mixture of 2,7-dinitrodibenzothiophene and its S-oxide. This suggests that a great difference in the reaction mechanism may exist between 4 and 1 or 3.

To our knowledge, there have been no reports so far on trifluoromethylation of carbanions, enol silyl ethers, a phosphine, and an iodide anion as mentioned above. Thus, the powervariable thio-and selenophenium salt system is expected to serve as widely applicable reagents for electrophilic trifluoromethylation.