Preparation of 6,13-Bis(trimethylsilyl)pentacene and Formation of Second-Ring Diels−Alder Adduct of Pentacene

Preparation of 6,13-Bis(trimethylsilyl)pentacene and Formation of Second-Ring Diels−Alder Adduct of Pentacene

6,13-Bis(trimethylsilyl)pentacene was synthesized by a coupling reaction of bicyclic dilithiobutadiene with diiodonaphthalene followed by aromatization. Diels−Alder reaction of 6,13-bis(trimethylsilyl)pentacene with dienophiles afforded the corresponding second-ring adducts. Elimination of two silyl...

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Veröffentlicht in:Journal of organic chemistry 2011-01, Vol.76 (1), p.293-296
Hauptverfasser: Jia, Zhiying, Li, Shi, Nakajima, Kiyohiko, Kanno, Ken-ichiro, Takahashi, Tamotsu
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung:6,13-Bis(trimethylsilyl)pentacene was synthesized by a coupling reaction of bicyclic dilithiobutadiene with diiodonaphthalene followed by aromatization. Diels−Alder reaction of 6,13-bis(trimethylsilyl)pentacene with dienophiles afforded the corresponding second-ring adducts. Elimination of two silyl groups gave the second-ring Diels−Alder adducts of parent pentacene.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo101774d