Unexpected cleavage of the N-N bond in the reactions of 3-pyrazolidinone-1-azomethine imines with HCN

Tetrahedron Letters

Volumn 48, Issue 30, 2007, Pages 5205-5208

  Pezdirc, Lidija ^a   Grošelj, Uroš ^a   Meden, Anton ^a   Stanovnik, Branko ^a   Svete, Jurij ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BENZAMIDE DERIVATIVE; HYDROGEN CYANIDE; IMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CYANIDE; PYRAZOLE DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; X RAY DIFFRACTION;

EID: 34250852818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.142     Document Type: Article

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24. General Procedure: All five reactions were carried out in a parallel synthesiser (Radley's Carousel 6 Reaction Station). Acetic acid (5 × 0.012 ml, 5 × 2 mmol) was added to the stirred mixtures of azomethine imines 4a-e (5 × 2 mmol), potassium cyanide (5 × 195 mg, 5 × 3 mmol), and methanol (5 × 8 ml) and the mixtures were stirred at rt for 3 h. The precipitates were collected by filtration, washed with ether, and dried in vacuo to give compounds 6a-d and 5e.
25. +).
26. +).
27. -1.
28. -1.
29. +).
30. Crystallographic data (excluding structure factors) for the structure of 6c in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 644415. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 0 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk.
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