Chapter 5c – Cyclohexadienes

Publisher Summary This chapter explains the methods of preparation of cyclohexadienes and their reactions. It also describes the chemistry of organometallic complexes of cyclohexadienes. The Birch reduction method, which is most widely used in the preparation of cyclohexadienes, is discussed. This process involves metal–ammonia reduction. Microbial oxidation of aromatic compounds, which involves oxidation of a variety of Pseudomonas putida UV4, results in the formation of cis-dihydrodiols of general structure. Preparation of cyclohexanones from cyclohexadienes using a modification of the Shapiro procedure is described in the chapter. Different reactions of cyclohexadienes, and the preparation and reactions of the metal complexes of cyclohexadienes are also described. There is considerable potential for application of the chemistry of cyclohexadiene-molybdenum complexes in organic synthesis. This is especially possible if useful methods are developed for controlled demetallation of the π-allyl-Mo (CO)2 complexes that result from nucleophile addition reactions.