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The photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxides
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dc.contributor.author | Broumidis, Emmanouil | |
dc.contributor.author | Thomson, Christopher G. | |
dc.contributor.author | Gallagher, Brendan | |
dc.contributor.author | Sotorríos, Lia | |
dc.contributor.author | McKendrick, Kenneth G. | |
dc.contributor.author | Macgregor, Stuart A. | |
dc.contributor.author | Paterson, Martin J. | |
dc.contributor.author | Lovett, Janet E. | |
dc.contributor.author | Lloyd, Gareth O. | |
dc.contributor.author | Rosair, Georgina M. | |
dc.contributor.author | Kalogirou, Andreas S. | |
dc.contributor.author | Koutentis, Panayiotis A. | |
dc.contributor.author | Vilela, Filipe | |
dc.date.accessioned | 2023-09-11T15:30:02Z | |
dc.date.available | 2023-09-11T15:30:02Z | |
dc.date.issued | 2023-09-22 | |
dc.identifier | 293803447 | |
dc.identifier | e2d32228-83e8-4b7a-a90e-4759cc7a3f5a | |
dc.identifier | 85172033929 | |
dc.identifier | 001065993400001 | |
dc.identifier | 37695021 | |
dc.identifier.citation | Broumidis , E , Thomson , C G , Gallagher , B , Sotorríos , L , McKendrick , K G , Macgregor , S A , Paterson , M J , Lovett , J E , Lloyd , G O , Rosair , G M , Kalogirou , A S , Koutentis , P A & Vilela , F 2023 , ' The photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxides ' , Organic Letters , vol. 25 , no. 37 , pp. 6907-6912 . https://doi.org/10.1021/acs.orglett.3c02673 | en |
dc.identifier.issn | 1523-7060 | |
dc.identifier.other | RIS: urn:3AD20D80477927C69422FEA5C0C5BD7E | |
dc.identifier.other | ORCID: /0000-0002-3561-450X/work/142499463 | |
dc.identifier.uri | https://hdl.handle.net/10023/28350 | |
dc.description | Funding: E.B. and C.G.T. are grateful to Heriot-Watt University and the EPSRC CRITICAT Centre for Doctoral Training (E.B. Ph.D. Studentship: EP/L016419/1, C.G.T Ph.D. Studentship: EP/LO14419/1) for funding and training. C.G.T. is grateful to the Heriot-Watt Annual Fund for financial support. P.A.K. and A.S.K. thank the University of Cyprus for the Internal Grant “Thiadiazine-Based Organic Photovoltaics”, and the Cyprus Research Promotion Foundation (Grant Nos. ΣΤΡΑΤΗΙΙ/0308/06, NEKYP/0308/02 ΥΓΕΙΑ/0506/19, and ΕΝΙΣΧ/0308/83). M.J.P. thanks the EPSRC for funding (Grant Nos. EP/T021675 and EP/V006746), and the Leverhulme Trust (Grant No. PG-2020-208). S.A.M. thanks the EPSRC for funding (Grant No. EP/T019867/1). | en |
dc.description.abstract | 1,2,6-Thiadiazines treated with visible light and 3O2 under ambient conditions are converted into difficult-to-access 1,2,5-thiadiazole 1-oxides (35 examples, yields of 39–100%). Experimental and theoretical studies reveal that 1,2,6-thiadiazines act as triplet photosensitizers that produce 1O2 and then undergo a chemoselective [3 + 2] cycloaddition to give an endoperoxide that ring contracts with selective carbon atom excision and complete atom economy. The reaction was optimized under both batch and continuous-flow conditions and is also efficient in green solvents. | |
dc.format.extent | 6 | |
dc.format.extent | 1946760 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Letters | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | AC | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | The photochemical mediated ring contraction of 4H-1,2,6-thiadiazines to afford 1,2,5-thiadiazol-3(2H)-one 1-oxides | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.institution | University of St Andrews. School of Physics and Astronomy | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.1021/acs.orglett.3c02673 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/L016419/1 | en |
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