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DOI: 10.1055/s-2007-966042
Synthesis of Highly Symmetrical Triptycene Tetra- and Hexacarboxylates
Publication History
Publication Date:
02 May 2007 (online)
Abstract
Two alternative procedures, both starting from easily accessible tetramethylanthracenes and employing the Diels-Alder addition as the key reaction step(s), have been examined in the synthesis of the title compounds.
Key words
carboxylic acids - Diels-Alder reactions - oxidations - triptycenes - arynes
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References
Rybáček J.; Rybáčková, M.; Høj, M.; Holý, P.; Bělohradský, M.; Kilså, K.; Nielsen, M. B., manuscript in preparation.
46a: 1H NMR (400 MHz, CDCl3): δ = 1.84 (s, 6 H), 2.35 (s, 6 H), 4.77 (s, 2 H), 6.98 (m, 2 H), 7.29 (m, 2 H), 7.42 (s, 2 H), 7.50 (s, 2 H). 6b: 1H NMR (400 MHz, CDCl3): δ = 1.83 (s, 6 H), 2.16 (s, 6 H), 2.34 (s, 6 H), 4.70 (s, 2 H), 7.10 (s, 2 H), 7.40 (s, 2 H), 7.46 (s, 2 H).
5Similar problems with regioselectivity are common in aryne addition to anthracenes, cf. ref 6. Steric hindrance to aryne approach due to methyls may account well for the different outcomes obtained with anthracenes 1 and 4 in Scheme [1] .