An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson

By Muriel Tomlinson

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Rev. XVI, 292. BADDELEY (1954) Modern aspects of the Friedel and Crafts reaction, Quart. Rev. vra, 355. BADGER (1954) The Structures and Reactions of Aromatic Compounds. P. BERLINER (1945) The Friedel and Crafts reaction with aliphatic dibasic acid anhydrides, Org. Reactions, vol. V, 229. BERLINER (1964) Electrophilic substitution reactions, Progress in Physical Organic Chemistry, vol. II, Interscience. DE LA MARE andRiDD (1959) Aromatic Substitution, Nitration and Halogenation. Butterworths. GiLLESPiE and MILLEN (1948) Aromatic nitration, Quart.

Rev. vra, 355. BADGER (1954) The Structures and Reactions of Aromatic Compounds. P. BERLINER (1945) The Friedel and Crafts reaction with aliphatic dibasic acid anhydrides, Org. Reactions, vol. V, 229. BERLINER (1964) Electrophilic substitution reactions, Progress in Physical Organic Chemistry, vol. II, Interscience. DE LA MARE andRiDD (1959) Aromatic Substitution, Nitration and Halogenation. Butterworths. GiLLESPiE and MILLEN (1948) Aromatic nitration, Quart. Rev. II, 277. GOULD (1959) Mechanism and Structure in Organic Chemistry, Holt, Rinehart, Winston, chap.

Orbitals, we can write not only (5) but also (5a) and (5b-5f) as well. (5c) (5d) (5e) (5f) In aniline and phenol the reactivity of their nuclei at the o- and /^-positions towards electrophilic reagents can be associated with these representations of their structures, and even in chlorobenzene, in spite of the -I effect of the chlorine atom, which slows the reaction rate down, it is clear that electrophilic reagents may be expected to attack o- and /7-positions. The -I effects of hydroxyl and aminogroups must be unimportant compared with the large effects of conjugation.

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