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CH (17) the p- and ö-positions in cinnamic acid greater stabilisation will result because the charge can then be delocalised into the side-chain as well as in the nucleus (17a-17d). Effect of the Reactivity of the Reagent on Orientation Finally the electrophilic power of the reagent also influences the proportions of isomers formed in aromatic substitutions. It is diffi­ cult to illustrate this by any comparisons involving or//zö-positions because steric effects complicate the issue, but meta:para ratios, where steric effects are comparable, are clearly dependent on the reagent.

NORMAN and TAYLOR (1965) Electrophilic Substitution in Benzenoid Compounds, Elsevier. OLAH (1963-5) Friedel and Crafts and Related Reactions, vols. I-V. Interscience. PRICE (1946) Alkylation of aromatic compounds by the Friedel-Crafts method, Org. Reac. ΙΠ, 1. Richters Organic Chemistry, vol. Ill, Mee. C. Lectures. C—C 52 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS ROBINSON (1934) Substitution in the benzene nucleus, /. Soc. Dyers Colourists, 65. RODD, Chemistry of Carbon Compounds, vol.

103) C6H5—N=N—OH ► C6H5· + N2 + OH are allowed to react with benzene biphenyl (8) is produced. e. a radical adds on to benzene to give a new stabilised radical (9a-9c); loss of a hydrogen atom, abstracted by some other radical, then restores the aromatic structure. There is no difference in the rate of reaction with isotopically labelled benzenes and so removal of the hydrogen atom seems to be the faster stage of the reaction. FURTHER READING See Further Reading references at the end of Chapter 3.

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