ANALYSIS OF SKELETAL REARRANGEMENT ROUTES IN THE TRICYCLO[4.2.2.0(2,5)]DECANE SYSTEM IN THE COURSE OF ELECTROPHILIC ADDITION-REACTIONSстатья
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Дата последнего поиска статьи во внешних источниках: 29 мая 2015 г.
Аннотация:Addition of electrophilic reagents to derivatives of tricyclo[4.2.2.0.(2,5)]deca-3,7-diene (1a-e) and tricyclo[4.2.2.0(2,5)]deca-3,7,9-triene (2) yields compounds with several new types of carbon skeleton. Detailed comparison of X-ray data for the reaction products revealed a variety of geometrical anomalies in their molecular structure, indicating that it may be subject to skeletal rearrangements. Reasonable multistep mechanisms for these rearrangements were suggested for the initial olefins by our ICAR computer program; the probability of these mechanisms was estimated by molecular mechanics calculations. This analysis suggests explanations for the predominant formation of major reaction products and for different rearrangement paths of the similar compounds 1 and 2.