Diels-Alder reactions of masked o-benzoquinones: new experimental findings and a theoretical study of the inverse electron demand case

Odón Arjona; Rocío Medel; Joaquín Plumet; Rafael Herrera; Hugo A Jiménez-Vázquez; Joaquín Tamariz

doi:10.1021/jo030307r

Diels-Alder reactions of masked o-benzoquinones: new experimental findings and a theoretical study of the inverse electron demand case

J Org Chem. 2004 Apr 2;69(7):2348-54. doi: 10.1021/jo030307r.

Authors

Odón Arjona¹, Rocío Medel, Joaquín Plumet, Rafael Herrera, Hugo A Jiménez-Vázquez, Joaquín Tamariz

Affiliation

¹ Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain.

PMID: 15049629
DOI: 10.1021/jo030307r

Abstract

Diels-Alder reactions of the masked o-benzoquinone (MOB) 2 with vinylene carbonate (3), the bicyclic derivatives 4, 5, and 6, and the intramolecular version of the 2-hydroxymethylfuran-MOB Diels-Alder reaction are described. In addition, a theoretical study of the Diels-Alder reactions of MOBs with enol and thioenol ethers is presented.