Ether formation from allylic alcohols catalyzed by samarium trichloride |
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| Authors: | Mohsen Ouertani Jacqueline Collin Henri B. Kagan |
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| Affiliation: | Unité de Recherche n° 255 associée au CNRS, Laboratoire de Synthèse Asymétrique Université Paris-Sud, 91405 OrsayFrance |
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| Abstract: | The behaviour of various allylic alcohols in the presence of catalytic amounts of SmCl3 (by heating in 1,2-dichloroethane) has been studied. Diallyl ethers are obtained in many cases in good yields. Mixed allyl alkyl ethers are also prepared if 2–5 equivalents of an aliphatic alcohol is present. The reactions are interpreted as proceeding through a pseudo allylic carbonium intermediate initiated by a preliminary complexation of the allyl hydroxyl to the samarium ion. |
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