By Muriel Tomlinson
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Additional info for An Introduction to the Chemistry of Benzenoid Compounds
When the aromatic structure is restored it is the chloride ion which departs. Convincing evidence for the participation of intermediates like (18a-18b) is provided by the action of potassium 46 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS ethoxide on 2,4,6-trinitroanisole and potassium methoxide on 2,4,6trinitrophenetole. An intermediate addition product (19a-19c), an cr MeO OEt I MeO OEt N02 VS> NO, (19a) (19b) (19c) anion, must be formed because acidification, after both reactions, produces a mixture of methoxy- and echoxytrinitrobenzene.
FURTHER SUBSTITUTION INTO SUBSTITUTED BENZENOID COMPOUNDS It soon became clear that the product of a benzene disubstitution reaction is generally either (a) mainly a mixture of ortho- and paraisomers, or (b) chiefly the meta-compound. It is even more obvious that the conditions necessary to bring about the reactions are often very different from those used for benzene itself. In general, substituents fall into three main classes. R,-CHO, - CN, etc. When these are present the main product is the weta-isomer, the reactions need more vigorous con ditions and proceed up to 107 times more slowly than the correspond ing reactions with benzene do: Friedel Crafts reactions do not occur at all when the above groups are present.
From an alcohol, reduc tion will not proceed. When a substituent is present, experiments show that the proton becomes attached to a carbon that is joined to a carbonyl group which can share the charge, but will be repelled from a carbon atom which carries electron releasing groups like -NMe2> -OMe> -CH3. This process (Birch reduction) can be used to prepare cyclohexenone (11) from anisole: the dihydrobenzene (10) is hydrolysed by acid because it is a vinyl ether. Rearranges (10) (11) Nuclei which carry carbonyl-groups as substituents can be reduced by less vigorous reagents.
An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson