Application of electrogenerated triphenylmethyl anion as a base for alkylation of arylacetic esters and arylacetonitriles and isomerization of allylbenzenes

Abstract

Phenylacetic esters and phenylacetonitriles were alkylated with alkyl halides, at the position α to an ester or nitrile, either at room temperature (20 °C) or at −78 °C, by making use of electrogenerated triphenylmethyl anion (trityl anion). Double-bond isomerization of allylbenzenes was also effectively accomplished by use of this electrogenerated base (EGB).

Isomerization of Allylbenzenes

“…In an interesting electrochemical isomerization procedure, Nakajima and co-workers demonstrated that the triphenylmethyl anion, generated by way of a one-electron reduction under electrolysis, was able to isomerize a number of topical arylallyl compounds 1 . β-Methylstyrenes 2 were successfully obtained including those derived from safrole 6 , estragole 7 , allylbenzene 3 , and 1-allyl-3,4-dimethoxybenzene 17 (Scheme gives the generalized summary).…”

Comparative Extraction of Aluminum Group Metals Using Acetic Acid Derivatives with Three Different-Sized Frameworks for Coordination

“…Tripodal 3 also exhibited an unexpected stoichiometry of 1:2 (3:In 3+ ). This can be explained by "allosteric coextraction", because while 3 provides only three acetic acid groups for neutralization of the In 3+ charge, it also provides a very active triphenylmethyl proton for the second In 3+ , which acts as carbon acid and has an estimated pK a value of 30 [55][56][57]. While very weak, the acid has sufficient strength to form a metal complex [58].…”

Proazaphosphatrane P(RNCH2CH2)3N (R=Me, i‐Pr)‐Catalyzed Isomerization of Allylaromatics, Allyl Phenyl Sulfide, Allyl Phenyl Sulfone, and bis‐Allylmethylene Double Bond‐Containing Compounds

“…[20] The electrogenerated triphenylmethyl anion acted as a base to isomerize allylaromatics. [21] Isomerization of allyl sulfides has been reported with NaOH or NaOEt, [22a, b] Pd(PCy 3 ) 2 (PCy 3 ¼ tricyclohexylphosphine), [22c] or tris(2,4-pentanedionate)ruthenium.…”