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Title: | Efficient [2+2] photocycloadditions under equimolar conditions by employing a continuous UV-flow reactor | Authors: | CONRADI, Matthias Horst JUNKERS, Tanja |
Issue Date: | 2013 | Publisher: | ELSEVIER SCIENCE SA | Source: | JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 259, p. 41-46 | Abstract: | The [2 + 2] photocycloaddition between maleimide and various alkenes was optimized in a simple custom-made UV flow reactor. While complete maleimide conversion is only achieved with excesses of at least 10 eq. of alkene and reaction times of 12-24 h in batch, complete reactions with yields in the range >98% could be obtained in 5 min in the flow reactor under strictly equimolar conditions. Functional alkenes carrying allyl, alcohol, amine and ether moieties were successfully conjugated in good yields under optimized reaction conditions. As is demonstrated, the reaction gains in flow most characteristics of a high-efficient reaction, making the process highly valuable for upscaled synthesis of maleimide conjugates. (C) 2013 Elsevier B.V. All rights reserved. | Notes: | [Conradi, Matthias; Junkers, Thomas] Univ Hassel, Inst Mat Res, Polymer React Design Grp, IMO, B-3590 Diepenbeek, Belgium. | Keywords: | [2 + 2]-cycloaddition; photochemistry; flow chemistry; functional group tolerance; photo-conjugation;[2+2]-Cycloaddition; Photochemistry; Flow chemistry; Functional group tolerance; photo-conjugation | Document URI: | http://hdl.handle.net/1942/17231 | ISSN: | 1010-6030 | e-ISSN: | 1873-2666 | DOI: | 10.1016/j.jphotochem.2013.02.024 | ISI #: | 000319089900006 | Rights: | © 2013 Elsevier B.V. All rights reserved. | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2014 |
Appears in Collections: | Research publications |
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