New rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole

作者：Sokolenko W A^*; Svirskaya N M; Rubailo A I

来源：Russian Chemical Bulletin, 2011, 60(8): 1776-1777.

DOI：10.1007/s11172-011-0265-x

• iodophenols
• 1-adamantanol
• alkylation
• trifluoroacetic acid
• electrophilic substitution
• the Reverden rearrangement

A reaction of 2-iodophenol and 2-iodoanisole with 1-adamantanol in trifluoroacetic acid gives the corresponding 4-(1-adamantyl) derivatives. Similar adamantylation of 4-iodophenol and 4-iodoanisole is accompanied by migration of the iodine atom from para- to ortho-position, giving 4,6-di(1-adamantyl)-2-iodophenol and 4-(1-adamantyl)-2-iodoanisole, respectively, as the reaction products.

• 出版日期2011-8