Novel synthesis of methylenecyclobutanols and 4-methylenetetrahydrofurans from gamma-oxide ylides.
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.
Okuma
Kentaro
K
Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan. kokuma@fukuoka-u.ac.jp
Kamahori
Yoshihiro
Y
Tsubakihara
Kimiko
K
Yoshihara
Kanami
K
Tanaka
Yuichiro
Y
Shioji
Kosei
K