Abstract
A convenient preparation of 8-(tolylmethyl)[2.2]metacyclophanes and 8,8′-(ethane-1,2-diyl)bis(16-methoxy[2.2]meta-cyclophane) using a cross-coupling reaction of 8-bromomethyl[2.2]metacyclophanes with tolylmagnesium bromides is described. The structures of these novel [2.2]metacyclophanes in solution are also discussed.
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