Δ2-1,2-diazetines : Regioselective acylation reactions and rearrangement into 4H-1,3,4-oxadiazines

Content Provider	Semantic Scholar
Author	Fleischhauer, Jan Beckert, Rainer Weston, Jennie Schmidt, Max Georg Flammersheim, H.-J. Goerls, Helmar
Copyright Year	2006
Abstract	Reaction of a 1-substituted Δ 2 -1,2-diazetine with acid chlorides or anhydrides resulted in the derivatives 3a,b,f that have been acylated at a ring position. On the other hand, trifluoroacetic anhydride yields a new 1,3,4-oxadiazine 4e under the same conditions. The structure of 4e could be confirmed by X-ray structural analysis. Acylated 1,2-diazetidines of type 3a,b can be nearly quantitatively transformed into 1,3,4-oxadiazines 4a,b by thermally induced ring-expansion reactions. Differential scanning calorimetry measurements provide evidence for a monomolecular mechanism in which a strong dependence of the acyl group on the rate of reaction is observed.
Starting Page	514
Ending Page	518
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1055/s-2006-926272
Volume Number	2006
Alternate Webpage(s)	http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-2006-926272.pdf
Alternate Webpage(s)	https://doi.org/10.1055/s-2006-926272
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article