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Generation and diels-alder reactions of α′-bromo-1,2-naphthoquinodimethane. a new phenanthrene synthesis

✍ Scribed by Gordon W. Gribble; Edward J. Holubowitch; Michael C. Venuti

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 193 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)83093-8

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✦ Synopsis

In 1959 Cava reported' that a,a'-dibromo-c-quinodimethane (z), generated by treatment of a,a,a',a'-tetrabromo-o-xylene (1) with NaI in warm DMF, --could be trapped by dienophiles to give 2,3-disubstituted naphthalenes. Cava's scheme is shown below with &phenylmaleimide as the trapping agent.

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