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Anson, Christopher E., Hartmann, Sascha, Kelsey, Richard D. and Stephenson, G. Richard 
ORCID: https://orcid.org/0000-0003-1487-9178
(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
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 |
| UEA Research Groups: | Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) |
| Depositing User: | Rachel Smith |
| Date Deposited: | 08 Jun 2011 11:29 |
| Last Modified: | 15 Aug 2023 13:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/31994 |
| DOI: | 10.1016/S0277-5387(99)00410-6 |
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