Home
Resources
Publications
Revisiting the Synthesis and Nucleophilic Reactivity of an Anionic Copper Superoxide Complex

Revisiting the Synthesis and Nucleophilic Reactivity of an Anionic Copper Superoxide Complex

Wilson D Bailey, Nicole L Gagnon, Courtney E Elwell, Anna C Cramblitt, Caitlin J Bouchey, William B Tolman

Inorg Chem. 2019 Apr 15;58(8):4706-4711.

PMID: 30901201

Abstract:

The addition of 1 equiv of KO2 and Kryptofix222 (Krypt) in CH3CN to a solution of LCu(CH3CN) [L = N, N'-bis(2,6-diisopropylphenyl)-2,6-pyridinecarboxamide] in tetrahydrofuran at -80 °C yielded [K(Krypt)][LCuO2], the enhanced stability of which enabled reexamination of its reactivity with 2-phenylpropionaldehyde (2-PPA). Mechanistic and product analysis studies revealed that [K(Krypt)][LCuO2] reacts with wet 2-PPA to form [LCuOH]-, which then deprotonates 2-PPA to yield the copper(II) enolate complex [LCu(OC═C(Me)Ph)]-. Acetophenone was observed upon workup of this complex or mixtures of KO2 and 2-PPA alone, in support of an alternative mechanism(s) to the one proposed previously involving an initial nucleophilic attack at the carbonyl group of 2-PPA.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP93538	2-Phenylpropionaldehyde		93-53-8	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: