A template effect in the synthesis of dibenzo‐14‐crown‐4 derivatives

A new series of 4‐substituted derivatives of dibenzo‐14‐crown‐4 including 4‐nitro‐DB14‐crown‐4 (2a), 4‐bromo‐DB14‐crown‐4 (2b), 4‐chloro‐DB14‐crown‐4 (2c) and 4‐formyl‐DB14‐crown‐4 (2d) has been synthesized with and without a lithium cation template. No matter with or without the template, a satisfactory correlation between the nature of the substituent group on the benzene ring and the reaction yield is observed. The larger σ values for the substituent groups gave lower yields.