Unprecedented formation of stable ketene-N,O-acetals and their rearrangement under basic conditions

Tetrahedron

Volumn 63, Issue 4, 2007, Pages 934-940

  Breuning, Matthias ^a   Häuser, Tobias ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Acylimidate; Benzimidic acid; Ketene N,O acetal; Rearrangement

Indexed keywords

ACETAL DERIVATIVE; AMIDE; CHLORINE DERIVATIVE; ESTER DERIVATIVE; KETENE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CHROMATOGRAPHY; MOISTURE; MOLECULAR STABILITY; ORGANIC CHEMISTRY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 33845419664     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.033     Document Type: Article

References (39)

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32. 8b,9a the meso-isomers can be enriched by fractional crystallization.
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37. Glutaryl dichloride 3b is a 1:1-mixture of dl-3b and meso-3b.
38. Several compounds are known in which an O-acyl-N-alkoxyalkylidene ketene-N,O-acetal function is incorporated into a hetarene (e.g., 6-alkoxypyridin-2-yl alkanoic acid esters) or a heterocycle with aromatic character (e.g., 6-oxo-6H-1,3-oxazin-4-yl alkanoic acid esters, 4-alkoxy-2-alkylidene-2H-oxazol-5-ones). To the best of our knowledge, compounds 9b-d are the only examples of stable ketene-N,O-acetals devoid of such an electronic stabilization.
39. 13C NMR signals were assigned by 2D experiments.