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Lewis‐Acid‐Catalyzed Reactions of Bis(4‐alkoxyphenyl)methanol with (Diarylmethylene)‐ and (Dialkylmethylene)cyclopropanes
Author(s) -
Yao LiangFeng,
Shi Min
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900546
Subject(s) - chemistry , cyclopentene , methanol , catalysis , organic chemistry , medicinal chemistry , lewis acids and bases , reaction conditions
Bis(4‐methoxyphenyl)methanol ( 2a ) can be transformed by BF 3 · OEt 2 ‐catalyzed reactions of (arylmethylene)cyclopropanes 1 to the corresponding polysubstituted cyclopentenes 3 as the major products along with methylenecyclobutanes and dienes as minor products. The reaction conditions are mild, yields are moderate to good. In the reactions of aliphatic methylenecyclopropanes with bis(4‐methoxyphenyl)methanol ( 2a ), cyclopentenes 3o – q were produced in good yields under the standard conditions. Interesting results were obtained from the reactions of 1‐[cyclopropylidene(4‐methoxyphenyl)methyl]‐4‐methoxybenzene ( 1e ) with bis(4‐alkoxyphenyl)methanols 2 : polysubstituted cyclopentene derivatives 5 were obtained in good yields under mild reaction conditions. Plausible reaction mechanisms based on the deuterium‐labeling and control experiments are proposed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)