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HERO ID
8406311
Reference Type
Journal Article
Title
Synthesis and Rearrangement of tert-Butylanthracenes
Author(s)
Peter, PF; Harvey, RG
Year
1977
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
42
Issue
14
Page Numbers
2407-2410
Language
English
DOI
10.1021/jo00434a013
Abstract
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.
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