67342-52-3Relevant articles and documents
Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception
Dev, Dharm,Kalita, Tapasi,Mondal, Tanmay,Mandal, Bhubaneswar
supporting information, p. 1427 - 1435 (2021/01/04)
A method for Beckmann rearrangement using ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino) acetate (o-NosylOXY) under microwave irradiation is reported. Ketoximes (19 examples) are converted to the corresponding amides/lactams with 69–97% yields in ~10 minutes without any Lewis acid or co-catalyst. This is an example of halogen-free organocatalytic Beckmann rearrangement. Nuclear magnetic resonance (NMR)- and high-resolution mass spectrometry (HRMS)-based detailed mechanistic investigation suggest that o-NosylOXY acts as an initiator. Such initiators are reported before based on density functional theory (DFT) calculations. However, we report here the HRMS signatures of two transient intermediates, the nitrilium ion and the nitrilium ion's dimeric species. Rigorous NMR-based investigation of the reaction mechanism is performed. Our results indicate that the reported Beckmann rearrangement proceeds via two consecutive rearrangements. (Figure presented.).
Synthetic method of azithromycin genotoxic impurities
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Paragraph 0032-0040, (2019/01/23)
The invention belongs to the field of chemical technology, and in particular relates to a synthetic method of azithromycin genotoxic impurities, wherein the impurity is acetone oxime-O-p-methyl sulfonic acid ester. The preparation method comprises the fol
Reaction of Trimethylsilyl Azide with C=N-O Bond
Nishiyama, Kozaburo,Miyata, Izumi
, p. 2419 - 2420 (2007/10/02)
Trimethylsilyl azide (TMSA) was reacted with an oxime ester or a Reissert salt in the presence of trimethylsilyl trifluoromethanesulfonate to give tetrazole derivative.The details of these reactions are examined.