Further investigations into the preparation and [4+2] cycloaddition reactions of vinyl norcaradiene derivatives

Abstract

Copyright © ARKAT USA, Inc The document attached has been archived with permission from the publisher.Norcaradiene derivatives derived from the copper-catalyzed intramolecular cyclopropanation reactions of 2-(5-vinyl-1,2,3,4-tetrahydronaphthalene) diazomethyl ketones have been prepared and submitted to Diels–Alder reactions with a range of dienophiles, including methyl acrylate, methyl 2-chloroacrylate, maleic anhydride and citraconic anhydride. The cycloaddition reactions gave better yields and were more selective when the vinyl norcaradienes were based on 8-methoxynaphthyl diazoketones.Lisa A. Buttle, Jonathan C. Morris, and Lewis N. Mande