A. Cox
1975
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Abstract
Publisher Summary This chapter provides an introduction to polycyclic compounds. Several compounds discussed in the chapter are the bicyclo [1.1.0] butane group, the bicycle [2.1.0] pentane group, the bicycle [3.1.0] hexane group, the bicycle [4.1.0] heptane group, the bicyclo [5.1.0] octane group, the bicycle [6.1.0] nonane group, and the bicyclo [2.2.0] hexane group. Bicyclo [1.1.0] butane reacts with benzyne mainly to give 3-phenylcyclobutene but some 1,3-cycloaddition product is also formed. 7,7-dimethylbicyclo [4.1.0] hexan-2-one is produced in the low-temperature reaction of cyclohexenone with diphenylsulfonium isopropylide. Derivatives of bicyclo [6.1.0] nonatriene for example, anti-9-methoxy-cis-bicyclo-[6.1.0] nona-2,4,6-triene, readily yield the all-cis-cyclononatetrenide anion on treatment with potassium, apparently in contravention of the orbital symmetry rules. Photochemically induced chlorination of bicycle [2.2.0] hexane proceeds inter alia with substitution at the bridgehead carbon in sharp contrast to reactions of bicyclo [2.1.0] pentanes and bicycle [1.1.0] butanes. Pyrolysis of the isomers of cis- and trans-6,7-dimethylbicyclo [3.2.0] heptane proceeds with only low specificity, probably by way of a radical intermediate, and irradiation of the tosylhydrazone, leads to a carbene which then collapses to a homofulvene.