dc.contributor.author |
Deadman, Benjamin J. |
|
dc.contributor.author |
O'Mahony, Rosella M. |
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dc.contributor.author |
Lynch, Denis |
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dc.contributor.author |
Crowley, Daniel C. |
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dc.contributor.author |
Collins, Stuart G. |
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dc.contributor.author |
Maguire, Anita R. |
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dc.date.accessioned |
2020-08-31T13:24:37Z |
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dc.date.available |
2020-08-31T13:24:37Z |
|
dc.date.issued |
2016-03-01 |
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dc.identifier.citation |
Deadman, B. J., O'Mahony, R. M., Lynch, D., Crowley, D. C., Collins, S. G. and Maguire, A. R. (2016) 'Taming tosyl azide: the development of a scalable continuous diazo transfer process', Organic & Biomolecular Chemistry, 14(13), pp. 3423-3431. doi: 10.1039/c6ob00246c |
en |
dc.identifier.volume |
14 |
en |
dc.identifier.startpage |
3423 |
en |
dc.identifier.endpage |
3431 |
en |
dc.identifier.issn |
1477-0520 |
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dc.identifier.uri |
http://hdl.handle.net/10468/10418 |
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dc.identifier.doi |
10.1039/c6ob00246c |
en |
dc.description.abstract |
Heat and shock sensitive tosyl azide was generated and used on demand in a telescoped diazo transfer process. Small quantities of tosyl azide were accessed in a 'one pot' batch procedure using shelf stable, readily available reagents. For large scale diazo transfer reactions tosyl azide was generated and used in a telescoped flow process, to mitigate the risks associated with handling potentially explosive reagents on scale. The in situ formed tosyl azide was used to rapidly perform diazo transfer to a range of acceptors, including beta-ketoesters, beta-ketoamides, malonate esters and beta-ketosulfones. An effective in-line quench of sulfonyl azides was also developed, whereby a sacrificial acceptor molecule ensured complete consumption of any residual hazardous diazo transfer reagent. The telescoped diazo transfer process with in-line quenching was used to safely prepare over 21 g of an alpha-diazocarbonyl in > 98% purity without any column chromatography. |
en |
dc.format.mimetype |
application/pdf |
en |
dc.language.iso |
en |
en |
dc.publisher |
Royal Society of Chemistry |
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dc.relation.uri |
https://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB00246C |
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dc.rights |
© The Royal Society of Chemistry 2016 |
en |
dc.subject |
Continuous flow synthesis |
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dc.subject |
C-H insertion |
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dc.subject |
Alpha-diazocarbonyl compounds |
en |
dc.subject |
Hetero-Wolff rearrangement |
en |
dc.subject |
Beta-oxo sulfoxides |
en |
dc.subject |
Organic synthesis |
en |
dc.subject |
Carbene insertion |
en |
dc.title |
Taming tosyl azide: the development of a scalable continuous diazo transfer process |
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dc.type |
Article (peer-reviewed) |
en |
dc.internal.authorcontactother |
Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie |
en |
dc.internal.availability |
Full text available |
en |
dc.date.updated |
2020-08-24T14:33:43Z |
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dc.description.version |
Accepted Version |
en |
dc.internal.rssid |
372342827 |
|
dc.internal.wokid |
000372795900011 |
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dc.contributor.funder |
Science Foundation Ireland
|
en |
dc.description.status |
Peer reviewed |
en |
dc.identifier.journaltitle |
Organic and Biomolecular Chemistry |
en |
dc.internal.copyrightchecked |
Yes |
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dc.internal.licenseacceptance |
Yes |
en |
dc.internal.IRISemailaddress |
a.maguire@ucc.ie |
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dc.internal.IRISemailaddress |
denis.lynch@ucc.ie |
en |
dc.relation.project |
info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/
|
en |
dc.identifier.eissn |
1477-0539 |
|