Stereochemistry at carbon of the cyclometalation of 8-(α-deuterioethyl)quinoline by palladium(II) salts

Organometallics

Volumn 15, Issue 20, 1996, Pages 4228-4234

  Holcomb, Harald L ^a   Nakanishi, Saburo ^b   Flood, Thomas C ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005992255     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9603068     Document Type: Article

References (38)

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18. Kinetic isotope effects in excess of 10 are well-known for proton/ deuteron transfer reactions and are generally attributed to tunneling through the reaction barrier by the lighter particle: Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980. Precedents for hydrogen tunneling involving metal centers are also becoming more numerous: Rosenberg, E. Polyhedron 1989, 8, 383. For example, a hydrogen kinetic isotope effect of 27 at 32 °C has been reported for migration of a metal hydride to a nitrogen ligand in a triosmium cluster: Anslyn, E. V.; Green, M.; Nicola, G.; Rosenberg, E. Organometallics 1991, 10, 2600.
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36. D of enantiomerically "pure" α-phenethyl chloride have varied widely: Ott, E. Chem. Ber. 1928, 61, 2124; 50.3°. Reference 7, 50.6°. Reference 8, 103.9°. Burwell, R. L.; Shields, A. D.; Hart, H. J. Am. Chem. Soc. 1954, 76, 908; 109°. Streitweiser, A.; Reif, L. J. Am. Chem. Soc. 1964, 86, 1988; 117°.
37. D of enantiomerically "pure" α-phenethyl chloride have varied widely: Ott, E. Chem. Ber. 1928, 61, 2124; 50.3°. Reference 7, 50.6°. Reference 8, 103.9°. Burwell, R. L.; Shields, A. D.; Hart, H. J. Am. Chem. Soc. 1954, 76, 908; 109°. Streitweiser, A.; Reif, L. J. Am. Chem. Soc. 1964, 86, 1988; 117°.
38. D of enantiomerically "pure" α-phenethyl chloride have varied widely: Ott, E. Chem. Ber. 1928, 61, 2124; 50.3°. Reference 7, 50.6°. Reference 8, 103.9°. Burwell, R. L.; Shields, A. D.; Hart, H. J. Am. Chem. Soc. 1954, 76, 908; 109°. Streitweiser, A.; Reif, L. J. Am. Chem. Soc. 1964, 86, 1988; 117°.