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HERO ID
7663222
Reference Type
Journal Article
Title
SOLUBLE CATALYSTS FOR IMPROVED PSCHORR CYCLIZATIONS
Author(s)
Wassmundt, FW; Kiesman, WF; ,
Year
1995
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Publisher
AMER CHEMICAL SOC
Location
WASHINGTON
Volume
60
Issue
1
Page Numbers
196-201
Language
English
DOI
10.1021/jo00106a034
Web of Science Id
WOS:A1995QC16000033
Abstract
Several improved catalysts for the Pschorr phenanthrene synthesis have been discovered; all are soluble substances which initiate free-radical reactions by electron donation and thereby shorten the reaction time and increase the yield. One technique with K4Fe(CN)(6) in water produced phenanthrene-9-carboxylic acid (6a) in 87% yield, but its application did not extend to substituted examples where the diazonium salt is less soluble in water. A more general procedure with ferrocene in acetone produced not only 6a but also substituted examples 6b-f in yields of 88-94%. A modification which avoids the isolation of diazonium salts was developed for occasional synthetic use.
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