Reaction of triflic anhydride with diazocompounds

✍ Scribed by Xavier Creary; You-Xiong Wang; William Gill

• Book ID: 104214879
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 252 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)74869-6

✦ Synopsis

Tnfllc anhydnde reacts with aryldtazomethanes to form predominantly os-stllbenes by a mechanism rnitiated by electron transfer from the dlazocompounds to the anhydnde Dlazocompounds are readily protonated under acldlc condttlons 1 They also undergo facile reactlon with electrophlles such as halogen,* t-BuOCI.3 and PhSCl 4 These reactlons proceed by InteractIon of the electrophlle with the nucleophllic carbon atom of the dlazocompound, followed by loss of molecular nitrogen and bondmg wtth available nucleophlle a-Dtazoketones react with the electrophilic reagent tnflic anhydnde, (CF3SO2)2O, to give blsenol tnflates by a mechanism mvolvlng sulfonatlon at oxygen of the nucleophlirc carbonyl group 5 R \ ,C=N2 E+ X-R-_C-E Ph-C-SO&F, d ? 1 bSO,CF, 2 3 Interest in such reactions of diazocompounds with electrophiles has prompted us to react phenyldiazomethane. 4. with tntliC annydflde It was initially antiCipated that sucn a reaction would lead to formation ot the a-SUlfOnyl tnllate