Novel alkylaluminium chloride promoted [2+2] cycloaddition reactions of styrenes with 1,4-naphthoquinones and bromoquinones: A facile route to orthoquinodimethane precursors

✍ Scribed by William S Murphy; Daniel Neville

• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 177 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)82974-7

✦ Synopsis

The first examples of a Lewis acid catalysed [2+2]cycloaddition between styrenes and naphthoquinones have been observed. The reactions of both methoxyl and acetoxylnaphthoquinones were both regio-and stereospecific. When m-methoxystyrene was employed a novel tetracycle was also formed, and by an unexpected mechanistic pathway. Extension to bromoquinones resulted ultimately in the formation of arylnaphthocyclobutenes, common precursors of the orthoquinodimethanes.