Novel Synthesis of Methylenecyclobutanols and 4-Methylenetetrahydrofurans from γ-Oxide Ylides
The Journal of Organic Chemistry2002Vol. 67(21), pp. 7355–7360
Citations Over TimeTop 22% of 2002 papers
Kentaro Okuma, Yoshihiro Kamahori, Kimiko Tsubakihara, Kanami Yoshihara, Yuichiro Tanaka, Kosei Shioji
Abstract
The reaction of delta-halo-gamma-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on delta-carbon of this ylide. Another novel approach toward the synthesis of 4-methylenetetrahydrofurans was achieved by the reaction of gamma-oxide ylides with paraformaldehyde.
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