DIAZO COMPOUNDS-66 5-(DIAZOMETHYL)-5H-DIBENZOCYCLOHEPTENES - INTERMEDIATES ON THE WAY TO NEW DIBENZOSEMIBULLVALENE AND DIBENZOCYCLOOCTENE SYNTHESES

Article abstract of DOI:10.1016/S0040-4020(01)87600-6

Electrophilic diazoalkane substitution of (silver diazomethyl)phosphoryl or mercury bis<(diazomethyl)-carbonyl> compounds (10a-c or 12a-c) with 5-chloro-5H-dibenzocycloheptene (6) furnishes the 5-(diazomethyl)-5H-dibenzocycloheptenes (8a-c or 13a-c).Copper(II) acetylacetonate-catalysed decomposition of these compounds in toluene results, in all cases, the formation of dibenzosemibullvalenes (17a-f).In addition, the dibenzocyclooctenes 16a-e and, in the cxase of 13c, the dibenzoheptefulvene 18f are formed.