Syntheses, Structures, and Dimerizations of Ferrocenyl-and Fluorenylideneallenes: Push− Pull Multiple Bonds?

…, CM Seward, H Müller-Bunz, MJ McGlinchey

Index: Banide, Emilie V.; Ortin, Yannick; Seward, Corey M.; Harrington, Laura E.; Mueller-Bunz, Helge; McGlinchey, Michael J. Chemistry - A European Journal, 2006 , vol. 12, # 12 p. 3275 - 3286

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Citation Number: 13

Abstract

9-(Ferrocenylethynyl) fluoren-9-ol (9) and SOCl2 form the head-to-head allene dimer (15), possessing a very long (∼ 1.65 Å) C (3)− C (4) bond linking the two spiro-bonded fluorenyl fragments; in contrast, 9 reacts with HBr to form the hexa-1, 2-dien-5-yne 17. Protonation of ferroceno [2, 3] inden-1-ol (25) and subsequent reduction yield the radical coupling dimer 29.