The ICAR program: Computer-assisted investigation of carbocationic rearrangements

The problem of computer-assisted generation of carbocationic rearrangements is considered. The formalized approach to the description of carbocationic transformations is presented and the ICAR program (Investigation of CArbocationic Rearrangements) is briefly described. The ICAR program combines the pure combinatorial methods of the generation of carbocationic transformations with a flexible system of empirical selection criteria. Main principles of constructive enumeration of rearranged pathways and examples of selection criteria are discussed. The results of the solution of several carbocationic problems are also briefly mentioned. For instance, it is shown that the well-known “adamantane-land” is incomplete and should be supplemented with new possible precursors of adamantane. The working PC-version of the ICAR program with user's manual is included on disk in this issue.