Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity

Cini, Melchior and Bradshaw, Tracey D. and Lewis, William and Woodward, Simon (2013) Cuprate addition to a 6-substituted pentafulvene: preparation of sec-alkyl substituted titanocene dichlorides and their biological activity. European Journal of Organic Chemistry, 2013 (19). pp. 3997-4007. ISSN 1099-0690

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Abstract

The copper-catalysed (10 mol-% CuBr·SMe2, CuCN·LiCl or CuI/PPh3) addition of RMgBr to the pentafulvene 1-(cyclopenta-2,4-dien-1-ylidenemethyl)-2-methoxybenzene allows the formation of cyclopentadienyl derivatives with α-CHR(2-MeOPh) sidechains (R = Me, Et, nBu, iBu, allyl, Ph) without H– transfer. The deprotonation of these sec-alkyl-substituted cyclopentadienyls followed by the addition of TiCl4 allows the isolation of TiCl2{η5-C5H4CHR(2-OMePh)} as rac/meso mixtures that show activity against human colon, breast and pancreatic cell lines (GI50 2.3–42.4 μM).

Item Type: Article
Schools/Departments: University of Nottingham UK Campus > Faculty of Science > School of Chemistry
Related URLs:
URLURL Type
http://www.interscience.wiley.com/Publisher
Depositing User: Woodward, Prof Simon
Date Deposited: 24 Jun 2014 11:33
Last Modified: 13 Sep 2016 18:17
URI: http://eprints.nottingham.ac.uk/id/eprint/3200

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