α-Arylamino Diazoketones
- Author(s)
- Laura Castoldi, Laura Ielo, Wolfgang Holzer, Gerald Giester, Alexander Roller, Vittorio Pace
- Abstract
Primary and secondary a- halomethyl diazoketones generated via Arndt- Eistert chem. with min. loading of diazomethane efficiently alkylate arom. amines in the presence of calcium oxide to furnish the corresponding a- arylamino diazoketones under full chemocontrol. Such a simple inorg. acid scavenger fully neutralizes the hydrohalic acid formed during the nucleophilic displacement which otherwise would immediately react to produce the corresponding a- haloketone. The methodol. can be further exploited in analogous acylation- type processes on secondary arylamino diazoketones. In depth spectroscopic (1H, 13C and 15N- NMR) and crystallog. analyses document interesting structural features of these previously unknown diazo derivs.
- Organisation(s)
- Department of Mineralogy and Crystallography, Core Facility Crystal Structure Analysis
- External organisation(s)
- Università degli Studi di Messina
- Journal
- The Journal of Organic Chemistry
- Volume
- 83
- Pages
- 4336-4347
- No. of pages
- 12
- ISSN
- 0022-3263
- DOI
- https://doi.org/10.1021/acs.joc.7b03134
- Publication date
- 03-2018
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 104015 Organic chemistry, 104026 Spectroscopy, 301207 Pharmaceutical chemistry, 105113 Crystallography
- Keywords
- ASJC Scopus subject areas
- Organic Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/2dee04c6-0a98-4b8b-be28-a53bcb13186e