Advances in Mass Spectrometry 1985. Parts A and B: Edited by J. F. J. Todd. Pp. 1661. Wiley, Chichester. 1986. £195.00

Abstract

The chapter presents a review that covers nonannelated and annelated eight-membered heterocycles containing one nitrogen. When heterocyclic rings are fused to the azocine, naming must not only provide for the location of fusion on the eight-membered ring, but also for fusion of the azocine on the other ring. When the eight-membered ring is part of a spiran, the compound is named as a spiroalkane with the position of the nitrogen denoted by “aza,” prefixed with a number. Preparative methods of azocines via ring closure, via ring expansion, and via cycloaddition and cycloreversion are described. Azocine is of theoretical interest because it is a heterocyclic analog of the 8π nonaromatic annulene cyclooctatetraene (COT). Although azocine itself is found to be quite unstable on the synthesis of azocine derivatives indicate that appropriately substituted compounds could be more stable. The picture of azocine vis-à-vis cyclooctatetraene is outlined in the chapter. Stereochemical studies of azocines are also discussed. The reactions of derivatives of partially and fully saturated eight-membered rings, including enantholactam, are described. Those that are of particular relevance to the azocine ring, such as transannular reactions, are discussed in greater detail. The chapter presents preparative methods, theoretical aspects, stereochemical considerations, reactions and applications of benzazocines, dibenzazocines, tribenzazocines, and other fused azocines.