Novel Synthesis of Methylenecyclobutanols and 4-Methylenetetrahydrofurans from γ-Oxide Ylides

The reaction of δ-halo-γ-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on δ-carbon of this ylide. Another novel approach toward th...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-10, Vol.67 (21), p.7355-7360
Main Authors: Okuma, Kentaro, Kamahori, Yoshihiro, Tsubakihara, Kimiko, Yoshihara, Kanami, Tanaka, Yuichiro, Shioji, Kosei
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:The reaction of δ-halo-γ-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on δ-carbon of this ylide. Another novel approach toward the synthesis of 4-methylenetetrahydrofurans was achieved by the reaction of γ-oxide ylides with paraformaldehyde.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0202435