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  Flexible synthesis of phenanthrenes by PtCl2-catalyzed cycloisomerization reaction

Fürstner, A., & Mamane, V. (2002). Flexible synthesis of phenanthrenes by PtCl2-catalyzed cycloisomerization reaction. Journal of Organic Chemistry, 67(17), 6264-6267. doi:10.1021/jo025962y.

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 Creators:
Fürstner, A.1, Author              
Mamane, V.1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: Readily available biphenyl derivatives containing an alkyne unit at one of their ortho positions are converted into substituted phenanthrenes upon exposure to catalytic amounts of either PtCl2, AuCl3, GaCl3, or InCl3 in toluene. This 6-endo- dig cyclization likely proceeds through initial a-coordination of the alkyne unit followed by interception of the resulting eta(2)-metal complex by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product except C-9. Moreover, the reaction is readily applied to the heterocyclic series as exemplified by the preparation of benzoindoles, naphthothiophenes as well as bridgehead nitrogen heterocycles.

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Language(s): eng - English
 Dates: 2002-08-23
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 19904
DOI: 10.1021/jo025962y
ISI: 000177559800064
 Degree: -

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Title: Journal of Organic Chemistry
  Alternative Title : J. Org. Chem.
Source Genre: Journal
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Pages: - Volume / Issue: 67 (17) Sequence Number: - Start / End Page: 6264 - 6267 Identifier: ISSN: 0022-3263