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A template effect in the synthesis of dibenzo‐14‐crown‐4 derivatives
Author(s) -
Chen C. S.,
Wang S. J.,
Wu S. C.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200358
Subject(s) - chemistry , substituent , yield (engineering) , crown (dentistry) , benzene , ring (chemistry) , lithium (medication) , stereochemistry , medicinal chemistry , organic chemistry , medicine , materials science , dentistry , metallurgy , endocrinology
Abstract 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.