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Aldol reactions of γ‐ and ϵ‐methylene in 5‐membered heteroaromatic compounds
Author(s) -
Lee Chang Kiu,
Gong Jin Soon,
Lee InSook Han
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320140
Subject(s) - chemistry , aldol reaction , potassium hydroxide , methylene , aldol condensation , intermolecular force , sodium cyanide , potassium , sodium hydroxide , potassium cyanide , organic chemistry , medicinal chemistry , cyanide , molecule , catalysis
5‐Methyl‐2‐thiophenecarboxaldehyde ( 1a ) and 3‐methyl‐2‐thiophenecarboxaldehyde ( 6 ) underwent intermolecular aldol reactions in which the methyl group behaved as active methylene in the presence of potassium cyanide. 5‐Methylfurfural ( 1b ) gave only 5,5′‐dimethylfuroin in the presence of potassium cyanide. But 1b formed an intermolecular aldol reaction product when sodium hydroxide was used.