On the reaction of (vinylimino)phosphorane and related compounds. 22. Syntheses and structural studies of methanocycloundeca[b]pyrrole ring systems

Novel 2-phenyl-6,11- and 2-phenyl-4,9-methanocycloundeca[b]pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3,8-methano[11]annulenone (3), a 10π-electron vinylogue of tropone, with [(1-phenylvinyl)imino]triphenulphosphorane (8c) and subsequent aromatization afforded 7,12- and 9,14-methano-15H-cycloundeca[b]indeno[2,3-d]pyrroles (15c and 16c), which also have methanocyclo-undeca[b]pyrrole ring systems