73611-79-7Relevant articles and documents
Synthetic Applications of Metal Halides.Conversion of Cyclopropylmethanols into Homoallylic Halides.
McCormick, J.P.,Barton, Donald L.
, p. 2566 - 2570 (1980)
Magnesium and beryllium halides in refluxing diethyl ether effect the transformation of cyclopropylmethanols into homoallylic halides,in contrast to several other metal halides and Lewis acid/nucleophile combinations which were examined.Magnesium bromide and iodide are particularly effective: conditions are mild,yields are high,and little or no byproducts are formed.Tertiary and benzylic alcohols are more reactive than secondary alcohols,while the latter are converted into E homoallylic halides with high stereoselectivity.Cyclopropylmethanol itself fails to react.In the cases of magnesium halide reactions with bicyclo-2-hexanol and bicyclo-2-heptanol,addition of an equimolar amount of zinc halide not only caused substantial rate enhancement but also increased regioselectivity.