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

N Kanomata, K Kamae, Y Iino…

Index: Kanomata, Nobuhiro; Kamae, Ken-ichi; Iino, Yukio; Nitta, Makoto Journal of Organic Chemistry, 1992 , vol. 57, # 20 p. 5313 - 5318

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Citation Number: 15

Abstract

Novel 2-phenyl-6, ll-and 2-phenyl-4, 9-methanocycloundeca [b] pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3, 8-methano [ll] annulenone (3), a 10welectron vinylogue of tropone, with [(1-phenylvinyl) imino] triphenylphosphorane (8a) and subsequent dehydrogenation. Similarly, the reaction of the annulenone 3 with (inden-3- y1imino) tributylphosphorane (8c) and subsequent aromatization afforded 7, 12-and 9, 14- ...