Syntheses with cyclobutadienes -15. Prismane / dewar benzene isomerization- x-ray crystal structure of tert-butyl 3,4,5-tri-tert-butyl-2,6-bis(trifluoromethyl)prismane-1-carboxylate
1986; Elsevier BV; Volume: 42; Issue: 19 Linguagem: Inglês
10.1016/s0040-4020(01)82084-6
ISSN1464-5416
AutoresHorst Wingert, Gerhard Maas, Manfred Regitz,
Tópico(s)Cancer Treatment and Pharmacology
ResumoThe heavily substituted Dewar benzene derivatives 3 and 5 merely yield the carboxylic acids 7 and 9 by loss of isobutene when heated to 150–200 °C; isomerization to the benzoic acid 8 is not at all observed. Prismane derivative 4, which is obtained from 5 photochemically, behaves analogously at 150°C, but the primarily formed acid 10 rearranges to the isomeric Dewar benzenecarboxylic acids 9 and 11 on prolonged heating at 150°C. The Dewar benzenecarboxylic esters 12 and 13, obtained from 9 and 11 by esterification with diazomethane, are transformed into prismane 15 photochemically.
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