LDA-catalyzed cycloisomerization of 2-(2-propynyloxy)ethyl iodides leading to 3-(iodomethylene)tetrahydrofurans |
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Authors: | Harada Toshiro Muramatsu Keiko Fujiwara Takayuki Kataoka Hiroshi Oku Akira |
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Affiliation: | Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. harada@chem.kit.ac.jp |
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Abstract: | LDA catalyzes cycloisomerization of 2-(2-propynyloxy)ethyl iodides to give 3-(iodomethylene)tetrahydrofurans. The reaction is proposed to proceed through a mechanism involving exo-cyclization of an alkynyllithium intermediate and protonation of the resulting alkylidene carbenoid by the starting iodide. [reaction: see text] |
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