X-ray crystallographic proof of regioselectivity in a nitrosobenzene cycloaddition, and development of a novel in situ heterocycloaddition trap for use during decomplexation of tricarbonyliron diene complexes in hippeastrine synthesis

Anson, C. E., Hartmann, S., Kelsey, R. D. and Stephenson, G. R. (2000) X-ray crystallographic proof of regioselectivity in a nitrosobenzene cycloaddition, and development of a novel in situ heterocycloaddition trap for use during decomplexation of tricarbonyliron diene complexes in hippeastrine synthesis. Polyhedron, 19 (5). pp. 569-571. ISSN 0277-5387

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Abstract

The heterocycloaddition reaction between nitrosobenzene and 2-methylcyclohexa-1,3-diene preferentially affords the regioisomer with the N-Ph group next to the methyl substituent, and this product has been characterised by X-ray crystallography. As a model study for a tricarbonyliron mediated route to the alkaloid hippeastrine, a 2-methyl-6-phenylcyclohexadiene analogue has been prepared from tricarbonyl(eta(5)-3-methylcyclohexadienyl) iron(1+) hexafluorophosphate(1-) and has been examined in the heterocycloaddition reaction. A novel in situ heterocycloaddition trapping procedure has been developed based on this chemistry. Tricarbonyl(eta(4)-2-methyl-6-phenylcyclohexadiene)iron(0) can be converted directly into the cycloadduct in this way by reaction with trimethylamine N-oxide in the presence of nitrosobenzene. (C) 2000 Elsevier Science Ltd All rights reserved.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 08 Jun 2011 11:29
Last Modified: 21 Apr 2020 21:12
URI: https://ueaeprints.uea.ac.uk/id/eprint/31994
DOI:

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