Ether formation from allylic alcohols catalyzed by samarium trichloride
作者:Mohsen Ouertani、Jacqueline Collin、Henri B. Kagan
DOI:10.1016/s0040-4020(01)91389-4
日期:1985.1
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 aliphaticalcohol is present. The reactions are interpreted as proceeding through a pseudo allylic carbonium intermediate initiated by a preliminary
Stereo- and regioselectivity in iodo diol formation from acyclic allylic alcohols
作者:A. Richard Chamberlin、Robert L. Mulholland
DOI:10.1016/0040-4020(84)80012-5
日期:1984.1
with a variety of acyclicallylicalcohols was investigated. Both aqueous iodine and acetylhypoiodite convert certain alkenols into iododiols and acetoxy iodoalcohols, respectively, with regio- and stereoselectivities as high as 99%. Protection of the alcohol group lowers the selectivity only slightly. Structural factors that control the regioselectivity ofiodohydrin formation in these substrates