The search for efficient intramolecular proton transfer from carbon: The kinetically silent intramolecular general base-catalysed elimination reaction of O-phenyl 8-dimethylamino-1-naphthaldoximes

Journal of Physical Organic Chemistry

Volumn 18, Issue 2, 2005, Pages 101-109

  Asaad, Nabil ^a   Davies, John E ^a   Hodgson, David R W ^a,b   Kirby, Anthony J ^a   Van Vliet, Liisa ^a   Ottavi, Laura ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Elimination; Intramolecular general base catalysis; Oxime; Proton transfer

Indexed keywords

CARBON; CATALYSIS; DATA REDUCTION; ISOMERS; MOLECULAR STRUCTURE; PROTONS; REACTION KINETICS;

ELIMINATION; INTRAMOLECULAR GENERAL BASE CATALYSIS; OXIME; PROTON TRANSFER;

PHENOLS;

EID: 12444319339     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.858     Document Type: Conference Paper

References (19)

1. Kirby AJ. Adv. Phys. Org. Chem. 1980; 17: 183-278.
2. Kirby AJ. Acc. Chem. Res. 1997; 30: 290-296; Hartwell E, Hodgson DRW, Kirby AJ. J. Am. Chem. Soc. 2000; 122: 9326-9327.
3. Kirby AJ. Acc. Chem. Res. 1997; 30: 290-296; Hartwell E, Hodgson DRW, Kirby AJ. J. Am. Chem. Soc. 2000; 122: 9326-9327.
4. Kirby AJ, Percy JM. J. Chem. Soc., Perkin Trans. 2 1989; 907-912.
5. Kirby AJ, O'Carroll F. J. Chem. Soc., Perkin Trans. 2 1994; 649-655.
6. Gulick AM, Hubbard BK, Gerlt JA, Rayment I. Biochemistry 2000; 39: 4590-4602; St. Maurice M, Bearne SL. Biochemistry 2000; 39: 26.
7. Gulick AM, Hubbard BK, Gerlt JA, Rayment I. Biochemistry 2000; 39: 4590-4602; St. Maurice M, Bearne SL. Biochemistry 2000; 39: 26.
8. Alder RW, Bowman PS, Steele WRS, Winterman DR. J. Chem. Soc., Chem. Commun. 1968; 723-724.
9. Hollfelder F. PhD Thesis, University of Cambridge, 1997.
10. Hodgson DRW, Kirby AJ, Feeder N. J. Chem. Soc., Perkin Trans. 1 1999; 949-954.
11. Cho BR, Cho NS, Lee SK. J. Org. Chem. 1997; 62: 2230-2233.
12. Cho BR, Chung HS, Cho NS. J. Org. Chem. 1998; 63:4685-4690.
13. More O'Ferrall, RA, O'Brien DM, Murphy DG. Can. J. Chem. 2000; 78: 1594-1612.
14. Stewart R. The Proton: Applications to Organic Chemistry. Academic Press: New York, 1985.
15. Kirby AJ, Percy JM. Tetrahedron 1988; 44: 6903-6910.
16. Dunitz JD. X-Ray Analysis and the Structure of Organic Molecules. Cornell University Press: Ithaca, NY, 1979; 373-375.
17. Grech E, Malarski Z, SawkaDobrowolska W, Sobczyk L. J. Phys. Org. Chem. 1999; 12: 313-318.
18. Kiefl C. Eur. J. Org. Chem. 2000; 3279-3286.
19. Sheldrick GM. SHELXS-97/SHELXL-97. University of Göttingen: Göttingen, 1997.