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- Title
Evaluation of benzthiazolidine-based formamidinium salts for the synthesis of penem-type β-lactams by uncatalysed carbonylation of acyclic diaminocarbenes.
- Authors
Jonek, Markus; Buhl, Hannes; Leibold, Michael; Bruhn, Clemens; Siemeling, Ulrich
- Abstract
The reaction of [iPr2N=CHCl]Cl with 2-phenylbenzthiazolidine (Ph-BtzH) and subsequent anion metathesis afforded the formamidinium salt [(Ph-Btz)CH(NiPr2)][PF6] ([1aH][PF6]). The reaction of [1aH][PF6] with (Me3Si)2NNa in the presence of grey selenium furnished the selenourea derivative 1aSe as trapping product of the acyclic diaminocarbene 1a. In the absence of selenium, a 2H-1,4-benzothiazine derivative (2) was obtained, which is an isomer of 1a, whose formation is plausibly initiated by deprotonation of [1aH]+ not at the cationic N2CH unit, but at the neighbouring PhCH position. CO was ineffective as trapping reagent for 1a. [1aH][PF6], 1aSe and 2 have been structurally characterised by X-ray diffraction.
- Subjects
CARBONYLATION; LACTAMS; SALT; X-ray diffraction; PROTON transfer reactions; SELENIUM
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2019, Vol 74, Issue 4, p365
- ISSN
0932-0776
- Publication type
Article
- DOI
10.1515/znb-2019-0017