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A Facile Synthesis of Oxiranes Possessing Three or Four Carbonyl Groups

[ Vol. 23 , Issue. 1 ]

Author(s):

Haruyasu Asahara*, Shuhei Kikuchi, Yuto Unno, Soichi Yokoyama, Kotaro Yoshioka, Shinki Tani, Kazuto Umezu and Nagatoshi Nishiwaki*   Pages 97 - 102 ( 6 )

Abstract:


Tri-carbonylated oxiranes were efficiently synthesized by condensing a vicinal tricarbonyl compound with α-bromoketones in the presence of a base. This protocol was applicable to α–bromo-β-keto esters to create tetra-carbonylated oxiranes, from which trifunctionalized bromoalkene was competitively formed. The ratio of these compounds was influenced by the solvent and reaction temperature.

Keywords:

Polycarboylated oxirane, polyfunctionalized bromoalkene, vicinal tricarbonyl compound, α-bromo ketone, oxetane intermediate, trifunctionalized bromoalkene.

Affiliation:

School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Kumiai Chemical Industry Co., Ltd. Fujikawa-cho, Ihara-gun, Shizuoka 421-3306, Kumiai Chemical Industry Co., Ltd. Fujikawa-cho, Ihara-gun, Shizuoka 421-3306, Kumiai Chemical Industry Co., Ltd. Fujikawa-cho, Ihara-gun, Shizuoka 421-3306, School of Environmental Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502

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