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An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson

By Muriel Tomlinson

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FIG. 6. FIG. 7. It is generally found that reaction rates are reasonably parallel to the stabilities of the intermediate σ-complexes, but are unrelated to 26 INTRODUCTION TO THE CHEMISTRY OF BENZENOID COMPOUNDS the stabilities of the π-complexes: this is the most convincing evidence that σ-complexes are necessarily involved kinetically in substitutions. There is, however, no certainty that π-complex formation is a neces­ sary prelude to substitution. 1 (Brown; Norman) illustrates this important point.

81,100. HASSELL and ROMMING (1962) Charge transfer spectra bonds in solids, Quart, Rev. XVI, 11. C. Lecture Series No. 5. MILLAR and SPRINGALL (1966) Sidgwick's Organic Chemistry of Nitrogen, Clarendon Press, pp. 397, 483. NORMAN, Principles of Organic Synthesis, Methuen, p. 553. PAUSON (1967) Organometallic Chemistry, Arnold.

Reduction of (5) with sodium dithionite produces dibenzene chromium (6) which (5) (6) THE ADDITION REACTIONS OF THE BENZENE NUCLEUS 55 is a surprisingly stable brown solid. It is soluble in benzene, can be sublimed in vacuo, and decomposes at about 300°. Ozonisation, reduction, and addition of halogens are examples of the second type of addition. Although the benzene ring is very stable to ordinary oxidising agents, ozone reacts slowly with benzene to form a triozonide, and boron trifluoride will catalyse the reaction.

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