Mesoionic 1,3-oxazinium olates. rearrangement to acylketenes and 3-azabicyclo[3.1.1]heptanetriones.
Metastable but isolable mesoionic 1,3-oxazinium 4-olates 9d-f undergo ring opening to acylketenes 10 at or near room temperature. The ketenes undergo intramolecular criss-cross [2 + 2] cycloaddition to afford 3-azabicyclo[3.1.1]heptanetriones 12. The structure of 12d was established by X-ray crystallography.
Sheibani
Hassan
H
Chemistry Building, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, Qld 4072, Australia.
Bernhardt
Paul V
PV
Wentrup
Curt
C
D001372:Aza Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D005030:Ethylenes / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D001372:Aza Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004791:Enzyme Inhibitors; D005030:Ethylenes; D006536:Heptanes; D007659:Ketones; D010078:Oxazines; D010080:Oxazoles; C008223:ketene