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Catalytic aerobic oxidative coupling of some simple phenols and natural phenanthrols with CuCl(OH).TMEDA
P L MAJUMDER, , M ROYCHOWDHURY
Published in INDIAN CHEMICAL SOC
2000
Volume: 77
   
Issue: 8
Pages: 389 - 393
Abstract
Aerobic oxidative coupling of phenol, catechol, resorcinol and pyrogallol with CuCl(OH).TMEDA as catalyst affords 2',4-dihydroxybiphenyl (1a), 3,3',4,4'-tetrahydroxybiphenyl (2a), 2,2',4,4'-tetrahydroxybiphenyl (3a) and 2,2',4,6'-tetrahydroxybiphenyl (4a) and 2',3,3',4,4',5-hexahydroxybiphenyl (5a), respectively, in moderate yields. Similar catalytic aerobic oxidative coupling of the naturally occurring phenanthrols, nudol (6a) [2,7-dihydroxy-3,4-dimethoxyphenanthrene], 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene (6b) and cirrhopetalin (7) [7-hydroxy-4-methoxy-2,3-methylenedioxyphenanthrene] with the same reagent gives the corresponding 1,1'-biphenanthryls 8a and 8c and the 8,8'-biphenanthryl 9a, respectively, in very good yields. All these reactions exhibit a high degree of regioselectivity.
About the journal
JournalJournal of the Indian Chemical Society
PublisherINDIAN CHEMICAL SOC
ISSN0019-4522
Open AccessNo