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8406311 
Journal Article 
Synthesis and Rearrangement of tert-Butylanthracenes 
Peter, PF; Harvey, RG 
1977 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
42 
14 
2407-2410 
English 
Dehydrogenation of a series of mono-and di-tert-butyldihydroanthracenes is investigated as a potential synthetic route to the corresponding tert-butylanthracenes. Synthesis of 1-and 2-tert-butylanthracene is accomplished through dehydrogenation with DDQ and o-chloranil, respectively. Dehydrogenations with the reagent trityl trifluoroacetate generated in situ from trityl alcohol in trifluoroacetic acid lead to rearrangement and disproportionation to afford anthracene, 2-tert-butylanthracene, and 2,6-di-tert-butylanthracene. Similar rearrangements of the fully aromatic tert-butylanthracenes occur in trifluoroacetic acid neat. Reaction of anthracene with tert-butyltrifluoroacetate affords 2,6-di-tert-butylanthracene directly in high yield. The mechanism of these reactions and structural assignments of the tert-butylarenes by NMR analysis are discussed. © 1977, American Chemical Society. All rights reserved.