An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson

By Muriel Tomlinson

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The reaction 56 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS may also be used with compounds like phenol and aniline to prepare cyclohexanol (7) and cyclohexylamine (8). OH σ ΝΗ 2 OH H 2 /Ni 100 atm. Q) Ni/H 2 100 atm. 175· ^ . g. g. 9) which combines with a proton and then with another electron to form an ion. The above reagents do not normally attack benzene because there is very little resonance stabilisation of the anionradical (9) to help to overcome the stability of the benzene nucleus.

R~~\ Ph- + (~\-^ OCH3 ° O Ph / \ Ph N 2 r-^-\ °* =N - X7^" ° ^ ~ A V x H . OCH 3 (34) H V LU, \ " O etc · + FURTHERIREADING AROTSKY and SYMONS (1967) Halogen cations, Quart. 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.

10. attracted to the carbon at which the inductive effect of the NMe* groups is felt least, but substitution occurs at the m-position because less energy is required to achieve the transition state for m-substitution. The fact that nitration of benzoic acid gives principally m-nitrobenzoic acid and yet nitration of cinnamic acid (17), in which the carboxyl group is conjugated with the nucleus through an ethylenic link, gives mainly o- and ^-substitution appears less anomalous 44 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS when the localisation energy method is employed.

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