Chapter 10 - Polycarbocyclic Compounds. Fused or Condensed Cyclic Systems

Abstract

Publisher Summary This chapter discusses the fused or condensed ring-systems compounds that include: the bicyclo[1.1.0]butane group, the bicylo[2.1.0]pentane group, the bicyclo[3.1.0]hexane group, the bicyclo[4.1.0]heptane group, the bicyclo[5.1.0]octane group, the bicyclo [6.1.0]nonane group, the bicyclo[7.1.0]decane group, bicyclo[2.2.0]hexane and related compounds, the bicyclo[3.2.0]heptane group, the bicyclo[4.2.0]octane group, the bicyclo[5.2.0]nonane group, the bicyclo[6.2.0]decane group, the bicyclo[3.3.0]octane (pentalane) group, the bicyclo[4.3.0]nonane (hydrindane) group, the bicyclo[5.3.0]decane group, the bicyclo[4.4.0]decane (decalin) group, the bicyclo[5.4.0]undecane group, the bicyclo[5.5.0]dodecane group, the bicyclo[6.6.0]tetradecane group, and highly condensed alicyclic systems. Many members of the group may be obtained by hydrogenation of aromatic compounds with the same skeleton. The bicyclo[4.4.0]decane (decalin) group is further described on the basis of stereochemical analysis and classified into saturated and unsaturated compounds. General methods of preparation, properties, and typical reactions of these compounds and their corresponding amino, alcohol, and carboxylic acid derivatives are also examined. The examples provided include decalins, decalols, decalylamines, decalones, octalins, and hexahydronaphthalenes or hexalins. The stereochemistry of the perhydrophenanthrenes is important because of its relevance to the structure of the steroids and higher terpenoids. The octalins are prepared as pairs by the pyrolysis of the methyl carbonates of the decalols.