Chiral recognition in silver(I) olefin complexes with chiral diamines. Resolution of racemic alkenes and NMR discrimination of enantiomers

Organometallics

Volumn 23, Issue 1, 2004, Pages 15-17

  Cucciolito, Maria E ^a   Flores, Germana ^a   Vitagliano, Aldo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; COORDINATION REACTIONS; CRYSTALLINE MATERIALS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SILVER COMPOUNDS; STEREOCHEMISTRY;

CHIRAL DIAMINES; CHIRAL RECOGNITION; ENANTIOMERS; SILVER OLEFIN COMPLEXES;

ORGANOMETALLICS;

EID: 1642496745     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0341653     Document Type: Article

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18. If diethyl ether is used to precipitate the complexes of hydrocarbon olefins, partial or even total loss of the olefin may take place by a displacement reaction.
19. 2).
20. It should be noted that in the case of the Cu(I) complexes, to prevent oxidation, nitrate could not be used as a counterion.
21. Silver can be easily and quantitatively recovered as pure metal by reduction of the precipitated AgI with Zn powder in 0.1 M aqueous HCl and successive removal of the excess Zn with 5 M aqueous HCl.
22. It is known that olefinic alcohols can form chelate adducts with silver ions; Novak, M.; Aikens, D. A.; Closson, W. D. Inorg. Nucl. Chem. Lett. 1974, 10, 1117-1121. Moreover, on the sole basis of inductive effects on the Ag-olefin bond, allylic alcohols would be expected to give less stable adducts than, for example, ethylene, which implicitly supports the existence of an O⋯Ag stabilizing interaction in their complexes.
23. 6
24. 3 salt was obtained. The corresponding trfilate salt does not lose ethylene under vacuum.
25. 13