Organometallics, 21 (24), 5433 -5436, 2002. 10.1021/om0204989 S0276-7333(02)00498-3
Web Release Date: November 1, 2002

Copyright © 2002 American Chemical Society

Synthesis of 1'-Substituted Derivatives of 1,2,3,4,5-Pentaphenylferrocene

David C. D. Butler and Christopher J. Richards*

Department of Chemistry, Queen Mary, University of London, Mile End Road, London, E1 4NS, U.K.

Received June 24, 2002

Abstract:

Pentaphenylferrocene was synthesized in 57% overall yield from 1-bromopentaphenylcyclopentadiene. Functionalization of the unsubstituted cyclopentadienyl ring using the Friedel-Crafts reaction gave 1'-formyl- and 1'-(2-chlorobenzoyl)-substituted derivatives. Hydrolysis of the latter provided the corresponding 1'-carboxylic acid. This was readily transformed via a modified Curtius rearrangement into 1'-amino-1,2,3,4,5-pentaphenylferrocene. This methodology also provided (5-aminocyclopentadienyl)(4-tetraphenylcyclobutadiene)cobalt and gave an improved synthesis of aminoferrocene.

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