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Photochemical synthesis of a 1,8-naphthoquinodimethane. Generation of a thermally accessible triplet

✍ Scribed by Pagni, R. M.; Watson, C. R.; Bloor, J. E.; Dodd, J. R.

Book ID
126120376
Publisher
American Chemical Society
Year
1974
Tongue
English
Weight
414 KB
Volume
96
Category
Article
ISSN
0002-7863

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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.