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Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification
- Source :
- Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2719-2730 (2016)
- Publication Year :
- 2016
- Publisher :
- Beilstein-Institut, 2016.
-
Abstract
- A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide (DMF) solvent to the α-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (PS-BEMP) as the suitable base, packed-bed microreactors (pressure-resistant stainless-steel columns) have been fabricated and operated to accomplish the chemoselective synthesis of aroylated α-hydroxy ketones and 2-benzoyl-1,4-diones (benzoin- and Stetter-like products, respectively) with a good level of efficiency and with a long-term stability of the packing material (up to five days).
Details
- Language :
- English
- ISSN :
- 18605397
- Volume :
- 12
- Issue :
- 1
- Database :
- Directory of Open Access Journals
- Journal :
- Beilstein Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.f66dfc9fed3146e3acc5c8206120459b
- Document Type :
- article
- Full Text :
- https://doi.org/10.3762/bjoc.12.268