UNUSUAL CHEMICAL BEHAVIOR OF 9,10-DIPROPYL-10-BORABICYCLODECA-2,4,7-TRIENE, HETEROANALOG OF (CH)(10) HYDROCARBONS

摘要

The title compound 1 selectively gives products with completely different carbon skeletons in various reactions. Thus, thermolysis of 1 provides tricyclic borane 4, oxidation leads to the compounds 5, 6 (in a 5:1 ratio) with cyclooctatriene structure, methanolysis followed by oxidation yields bicyclic alcohol 7, and the reaction of 1 with acetone leads to the product with the cycloheptadiene skeleton 8. Such unusual chemical behavior of 1 can be rationalized by its coexistense with minor valence tautomers 12, 17, 18, 22. [References: 17]