Ritter Reactions between Alcohols and Acetonitrile Mediated by the Conducting Polymer Poly-(3,4-ethylenedioxy Thiophene) (PEDOT)

Abstract

Herein, we report new reactivity of the conducting polymer, poly-(3,4-ethylenedioxy thiophene) (PEDOT), where PEDOT mediates a Ritter reaction between alcohols and acetonitrile. The yields were variable and in most cases competitive with results obtained using sulfuric acid. Attempts at a stoichiometric reaction between benzonitrile and diphenylmethanol are also reported herein. Finally, described here are preliminary mechanistic studies that suggest PEDOT is behaving as an alcohol-selective or specific Lewis acid.

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GRAPHICAL ABSTRACT

Keywords:

• Alcohol
• amide
• conducting polymer
• PEDOT
• Ritter

Notes

^a 8 and 9 were not separated during purification. Ratios as determined by ¹H NMR integration are 4:1 of 8/9 (% calculated).

^b 5 and 8 were obtained as an inseparable mixture. Ratios as determined by ¹H NMR integration are 2:1 of 5/8 for entries 2 and 4 (% calculated).

Note. ND, not detected.