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Ether formation from allylic alcohols catalyzed by samarium trichloride

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
41
Issue
18
Identifiers
DOI: 10.1016/s0040-4020(01)91389-4

Abstract

Abstract The behaviour of various allylic alcohols in the presence of catalytic amounts of SmCl 3 (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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