Stuart G. Collins

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Organization: University College Cork , Ireland
Department: Department of Chemistry
Title: Lecture(PhD)

TOPICS

Co-reporter:Patrick G. McCaw, Naomi M. Buckley, Kevin S. Eccles, Simon E. Lawrence, Anita R. Maguire, and Stuart G. Collins
The Journal of Organic Chemistry April 7, 2017 Volume 82(Issue 7) pp:3666-3666
Publication Date(Web):March 8, 2017
DOI:10.1021/acs.joc.7b00172
Diazo transfer to β-keto sulfoxides to form stable isolable α-diazo-β-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived β-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile, and potential to scale up.
Co-reporter:Rosella M. O'Mahony;Denis Lynch;Hannah L. D. Hayes;Eilís Ní Thuama;Philip Donnellan;Roderick C. Jones;Brian Glennon;Anita R. Maguire
European Journal of Organic Chemistry 2017 Volume 2017(Issue 44) pp:6533-6539
Publication Date(Web):2017/12/01
DOI:10.1002/ejoc.201700871
The hazardous diazo transfer reagent mesyl azide has been safely generated and used in situ for continuous diazo transfer as part of an integrated synthetic process with an embedded safety quench. Diazo transfer to β-keto esters and a β-ketosulfone was successful. In-line phase separation, by means of a continuous liquid–liquid separator, enabled direct telescoping with a thermal Wolff rearrangement.
Co-reporter:Elaine Tarrant, Claire V. O'Brien and Stuart G. Collins  
RSC Advances 2016 vol. 6(Issue 37) pp:31202-31209
Publication Date(Web):22 Mar 2016
DOI:10.1039/C6RA03678C
A very mild, efficient and green method has been developed for diazo transfer to a range of β-ketoesters using polystyrene-supported benzenesulfonyl azide, water as solvent and a catalytic amount of base. This methodology eliminates the need for a standard work up and purification which is usually required to remove the sulfonamide by-product from the reaction.
Co-reporter:Patrick G. McCaw;Naomi M. Buckley;Anita R. Maguire
European Journal of Organic Chemistry 2016 Volume 2016( Issue 9) pp:1630-1650
Publication Date(Web):
DOI:10.1002/ejoc.201501538

Abstract

This review focuses on the synthesis and reactivity of thioketone S-oxides (sulfines). Sulfines have been long established as being reactive intermediates of high interest and with potential for wide application in organic synthesis. The review will cover many aspects of sulfines: the first section looks at the different routes to the synthesis of these compounds with a detailed look at more recently developed routes; the second section details the scope of reactivity of these types of compounds and how they are useful in synthetic organic chemistry with a particular look at cycloaddition and nucleophilic addition reactions.

Co-reporter:Roisin O’Keeffe, Olivia Kenny, Nigel P. Brunton, Mohammad B. Hossain, Dilip K. Rai, Peter W. Jones, Nora O’Brien, Anita R. Maguire, Stuart G. Collins
Bioorganic & Medicinal Chemistry 2015 23(9) pp: 2270-2280
Publication Date(Web):
DOI:10.1016/j.bmc.2015.02.034
Co-reporter:Dr. Benjamin J. Deadman;Dr. Stuart G. Collins; Anita R. Maguire
Chemistry - A European Journal 2015 Volume 21( Issue 6) pp:2298-2308
Publication Date(Web):
DOI:10.1002/chem.201404348

Abstract

The synthetic utilities of the diazo and diazonium groups are matched only by their reputation for explosive decomposition. Continuous processing technology offers new opportunities to make and use these versatile intermediates at a range of scales with improved safety over traditional batch processes. In this minireview, the state of the art in the continuous flow processing of reactive diazo and diazonium species is discussed.

Co-reporter:Stuart G. Collins, Orlagh C. M. O'Sullivan, Patrick G. Kelleher and Anita R. Maguire  
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 10) pp:1706-1725
Publication Date(Web):10 Jan 2013
DOI:10.1039/C3OB27061K
Diazo transfer adjacent to a sulfoxide moiety to provide stable, isolable α-diazo-β-oxo sulfoxides has been achieved. Use of monocyclic and bicyclic sulfoxide precursors is critical in enabling isolation of stable derivatives, through introduction of conformational constraint, while acyclic α-diazo-β-oxo sulfoxides are too labile to isolate and characterize.
Co-reporter:Stuart G. Collins, Orlagh C. M. O'Sullivan, Patrick G. Kelleher and Anita R. Maguire
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 10) pp:NaN1725-1725
Publication Date(Web):2013/01/10
DOI:10.1039/C3OB27061K
Diazo transfer adjacent to a sulfoxide moiety to provide stable, isolable α-diazo-β-oxo sulfoxides has been achieved. Use of monocyclic and bicyclic sulfoxide precursors is critical in enabling isolation of stable derivatives, through introduction of conformational constraint, while acyclic α-diazo-β-oxo sulfoxides are too labile to isolate and characterize.
Hexanoic acid, 2-diazo-3-oxo-, ethyl ester
3-Thiomorpholinone, 5,6-diphenyl-, trans-(±)-
1,4-Benzoxathiin-2(3H)-one, hexahydro-, (4aS-trans)-
2-Octanone, 1-(methylsulfinyl)-
Acetic acid, (butylsulfonyl)-, ethyl ester
1,4-Benzoxathiin-2(3H)-one, hexahydro-, (4aR,8aS)-
THYMIDINE, 3-BENZOYL-
1,4-Oxathian-2-one, 5,6-diphenyl-, trans-(±)-
3-Thiomorpholinone, 5,6-diphenyl-, cis-(±)-
Ethanone, 2-(dodecylsulfinyl)-1-phenyl-