Highly Stable Keto-Enamine Salicylideneanilines

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3823-3826

  Chong, Jonathan H ^a   Sauer, Marc ^a   Patrick, Brian O ^a   MacLachlan, Mark J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIFORMYLPHLOROGLUCINOL; ALCOHOL DERIVATIVE; ANILINE DERIVATIVE; ENAMINE; KETOENAMINE; TRIFORMYLPHLOROGLUCINOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; ROOM TEMPERATURE; SOLID STATE; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0242712861     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0352714     Document Type: Article

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43. All known examples have ethylenedithiolate substituents. See: (a) Gompper, R.; Kutter, E. Chem. Ber. 1965, 98, 1365. (b) Kimura, M.; Watson, W. H.; Nakayama, J. J. Org. Chem. 1980, 45, 3719. (c) Coffin, M. A.; Bryce, M. R.; Clegg, W. J. Chem. Soc. Chem. Commun. 1992, 401. (d) Mono, S.; Pritzkow, H.; Sundermeyer, W. Chem. Ber. 1993, 126, 2111.
44. All known examples have ethylenedithiolate substituents. See: (a) Gompper, R.; Kutter, E. Chem. Ber. 1965, 98, 1365. (b) Kimura, M.; Watson, W. H.; Nakayama, J. J. Org. Chem. 1980, 45, 3719. (c) Coffin, M. A.; Bryce, M. R.; Clegg, W. J. Chem. Soc. Chem. Commun. 1992, 401. (d) Mono, S.; Pritzkow, H.; Sundermeyer, W. Chem. Ber. 1993, 126, 2111.
45. All known examples have ethylenedithiolate substituents. See: (a) Gompper, R.; Kutter, E. Chem. Ber. 1965, 98, 1365. (b) Kimura, M.; Watson, W. H.; Nakayama, J. J. Org. Chem. 1980, 45, 3719. (c) Coffin, M. A.; Bryce, M. R.; Clegg, W. J. Chem. Soc. Chem. Commun. 1992, 401. (d) Mono, S.; Pritzkow, H.; Sundermeyer, W. Chem. Ber. 1993, 126, 2111.
46. F = -96.0 and -25.0 kJ/mol (keto more stable), respectively. AM1 is known to give good estimates of energies where strong hydrogen bonding is present, as in compounds 6. Geometries predicted by all three methods were similar.