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Intramolecular cyclization of nerol and the related (z)-allylic alcohols by means of TiCl4-PhNHMe complex. Synthesis of nezukone
Authors:Tadashi Saito  Akira Itoh  Koichiro Oshima  Hitosi Nozaki
Institution:Department of Industrial Chemistry, Faculty of Engineering Kyoto University, Yoshida, Kyoto 606, Japan
Abstract:Nerol is cyclized to terpinyl chloride or bromide in the presence of TiX4-PhNHMe (1:1) complex in dichloromethane at ?23 °C, while cyclization of (Z)-allylic alcohols CH2=CR-CH2CH2CMe=CHCH2OH (R = H, Me, Cl) produces seven-membered ring products in fair yields.
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