Direct Synthesis of N-Arylquinone Imine Acetals and Quinol Imines from Acetals

M Carmen Carreño; Juan M Cuerva; María Ribagorda; Antonio M Echavarren

doi:10.1002/(SICI)1521-3773(19990517)38:10<1449::AID-ANIE1449>3.0.CO;2-M

Direct Synthesis of N-Arylquinone Imine Acetals and Quinol Imines from Acetals

Angew Chem Int Ed Engl. 1999 May 17;38(10):1449-1452. doi: 10.1002/(SICI)1521-3773(19990517)38:10<1449::AID-ANIE1449>3.0.CO;2-M.

Authors

M Carmen Carreño¹, Juan M Cuerva¹, María Ribagorda¹, Antonio M Echavarren¹

Affiliation

¹ Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, E-28049 Madrid (Spain), Fax: (+349) 1-397-3966.

Abstract

In the absence of any added acidic catalyst quinone acetals as well as simple ketone and aldehyde acetals react with a variety of substituted anilines to form imines [Eq. (a)]. Contrary to what is expected from arguments based on their nucleophilicity, the most reactive anilines are those bearing electron-withdrawing groups.

Keywords: Acetals; Quinones; Radical ions; Schiff bases.