Facile C-N cleavage in a series of bridged lactams

Journal of the American Chemical Society

Volumn 127, Issue 13, 2005, Pages 4552-4553

  Lei, Yao ^a   Wrobleski, Aaron D ^a   Golden, Jennifer E ^a   Powell, Douglas R ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; LACTAM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; CONFORMATION; HYDROGENOLYSIS; HYDROLYSIS; REACTION ANALYSIS; REDUCTION; X RAY ANALYSIS;

AMIDES; LACTAMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 16844362083     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050214m     Document Type: Article

References (28)

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23. The identity of 1 was confirmed by making a bis-bromobenzoylated analogue that was subjected to X-ray analysis (Supporting Information).
24. 2-NC(O) bond in a [2.2.2]bicyclic lactam has been attributed to carbocation formation: Levkoeva, E. I.; Nikitskaya, E. S.; Yakhontov, L. N. Dokl. Akad. Nauk SSSR, 1970, 192, 342-345. In contrast, another twisted amide incorporating a tert-butyl proline moiety underwent clean hydrogenation with Pd/C in MeOH without fragmentation: Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474-2484.
25. 2-NC(O) bond in a [2.2.2]bicyclic lactam has been attributed to carbocation formation: Levkoeva, E. I.; Nikitskaya, E. S.; Yakhontov, L. N. Dokl. Akad. Nauk SSSR, 1970, 192, 342-345. In contrast, another twisted amide incorporating a tert-butyl proline moiety underwent clean hydrogenation with Pd/C in MeOH without fragmentation: Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474-2484.
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28. 6-ethanol, the same results were obtained.