Chemistry of isoindoles

Isoindole (1) and its analogs, isobenzofuran (2) and isothianaphthene (3), have attracted considerable theoretical and synthetic interest. -Of the jjarent heterocycles, only isothianaphthene (3) has proved sufficiently stable for isolation, - although both (1) and (2) have been detected as transient species, and it seems likely that a more complete characterization will be forthcoming with improved experimental techniques. This review is concerned with the chemistry of... 

The tenth volume of this serial publication comprises six chapters, four of which deal with the general chemistry of a specific group of heterocyclic compounds pyridopyrimidines (W. J. Irwin and D. G. VVibberley), benzofuroxans (A. J. Boulton and P. B. Ghosh), isoindoles (J. D. White and M. E. Mann), and pyrylium salts (A. T. Balaban, W. Schroth, and G. Fischer). The remaining chapters are concerned with indole Grignard reagents (R. A. Heacock and S. Kasparek) and with cyclic hydroxamic acids (J. B. Bapat, D. St. C. Black, and R. C. Brown).The international flavor of the publication is preserved our contributors come from six countries in three continents. 

A synthesis of highly-substituted tetracenes was developed starting from isoindole (benzo[c]pyrrole) <06OL273>. For example, treatment of dibromonaphthalene 87 with phenyllithium in the presence of isoindole 86 followed by deamination of the intermediate cycloadduct provided tetracene 88. Separately, the synthesis and cycloaddition chemistry of oxadisilole-fused isoindoles was investigated <06SL2510>. 

Derivatives of the naphthalen-l,4 -imine ring system (2) have become available only since the discovery of cycloaddition reactions of benzyne, on the one hand, and the recent rapid development of isoindole chemistry on the other. 

The chemistry of the o-quinonoidal heterocycles benzo[c] indole (isoindole, 1) and benzo[< ]thiophene (2) has been previously reviewed in this... 

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