Additions of Allylic Grignard Reagents to o-Allylphenol

Article abstract of DOI:10.1021/jo00332a003

Reactions of o-allylphenol (1a) with allylmagnesium chloride or bromide furnished 6-(o-hydroxyphenyl)-1-hexene (2a) and 4-methyl-5-(o-hydroxyphenyl)-1-pentene (3a), products resulting from both possible orientations of addition.A reaction of 1a and (2-methyl-2-propenyl)magnesium chloride gave only 6-(o-hydroxyphenyl)-2-methyl-1-hexene (2b).From comparisons with reactions of allylmagnesium chloride with o-allylanisole and allylbenzene, it is concluded that the metalated phenolic hydroxyl group, even though relatively remote from the double bond, assists the additions to 1a.