Title |
Taming tosyl azide: the development of a scalable continuous diazo transfer process
|
---|---|
Published in |
Organic and Biomolecular Chemistry, January 2016
|
DOI | 10.1039/c6ob00246c |
Pubmed ID | |
Authors |
Benjamin J. Deadman, Rosella M. O'Mahony, Denis Lynch, Daniel C. Crowley, Stuart G. Collins, Anita R. Maguire |
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 β-ketoesters, β-ketoamides, malonate esters and β-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 α-diazocarbonyl in >98% purity without any column chromatography. |
Mendeley readers
Geographical breakdown
Country | Count | As % |
---|---|---|
United Kingdom | 1 | 2% |
Spain | 1 | 2% |
Ireland | 1 | 2% |
Unknown | 60 | 95% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Ph. D. Student | 16 | 25% |
Researcher | 7 | 11% |
Student > Bachelor | 6 | 10% |
Student > Master | 4 | 6% |
Other | 1 | 2% |
Other | 5 | 8% |
Unknown | 24 | 38% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 31 | 49% |
Chemical Engineering | 2 | 3% |
Unspecified | 1 | 2% |
Agricultural and Biological Sciences | 1 | 2% |
Pharmacology, Toxicology and Pharmaceutical Science | 1 | 2% |
Other | 2 | 3% |
Unknown | 25 | 40% |