Preparative Organic Chemistry
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ChemInform Abstract: Novel Generation of o-Quinone Methides on the Basis of Lewis Acid Catalyzed 1,4-Dithiolation of o-(1-(Alkylthio)alkyl)phenols.
First published: September 11, 1990
Abstract
Treatment of 1-(alkylthio)alkylphenols with Lewis acids represents a simple and mild procedure to generate o-quinone methides such as (III) by a 1,4-dethiolation process.
ChemInform Abstract
Treatment of 1-(alkylthio)alkylphenols with Lewis acids represents a simple and mild procedure to generate o-quinone methides such as (III) by a 1,4-dethiolation process. The methides are coupled in situ with various dienophiles as outlined in the reaction scheme. Treatment of the o-citronellylphenol (XIII) with BF3·Et2O leads to the formation of the o-quinone methide (XIV) bearing an olefin moiety which undergoes intramolecular cycloaddition reaction, yielding the hexahydrodibenzopyran (XV).
