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Rev. II, 277. GOULD (1959) Mechanism and Structure in Organic Chemistry, Holt, Rinehart, Winston, chap. 11. HAMMOND and HAWTHORNE (1956) Steric effects in aromatic substitution, Steric Effects in Organic Chemistry, edited by Newman, Wiley. HEY (1967) Arylation of aromatic compounds, Advances in Free Radical Chemis­ try, vol. 2, 47. , McGraw-Hill, chaps. 16 and 17. C. Lecture Series, No. 2. NORMAN (1968) Principles of Organic Synthesis, Methuen, chaps. 11 and 12. NORMAN and TAYLOR (1965) Electrophilic Substitution in Benzenoid Compounds, Elsevier.

While benzene itself will not form any crystal­ line complexes of this type, alkylbenzenes such as mesitylene will do so with the more powerful complexing agents. Formula (2) repre­ sents the mesitylene-benzotrifuroxan complex. (2) ^-Complexes of benzene with hydrogen chloride and with iodine have been mentioned earlier (p. 21). Hydrogen chloride dissolves in 53 54 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS benzene at low temperatures to provide a 1:1 complex usually rep­ resented by (3).

Substitutions predominate. DISUBSTITUTION IN BENZENOID COMPOUNDS 37 When the group attracts the π-electrons from the benzene ring (mArX -raAlkX) is negative and substitution occurs mainly in the ra-position. FURTHER CONSIDERATION OF THE MECHANISM OF AROMATIC SUBSTITUTION Substitution into a benzene nucleus which already carries a sub­ stituent must proceed by a path related to that already described for benzene itself, but the presence of the substituent will clearly affect the stability of the transition states and the Wheland intermediate, and from what has been said above, it is obvious that the effect of a substituent will not be the same at all positions on the nucleus.

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