Photosolvolysis reactions of 3-alkoxypyridinium tetrafluoroborate salts

Tetrahedron

Volumn 55, Issue 19, 1999, Pages 6183-6204

  Penkett, Clive S ^a   Simpson, Iain D ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

Alkoxypyridinium; Aziridines; Cyclopentanone; Ketal formation; Photochemistry; Tetrafluoroborate

Indexed keywords

3 ALKOXYPYRIDINIUM TETRAFLUOROBORATE; 3 HYDROXY 6 METHYLPYRIDINE; 3 HYDROXYPYRIDINE; ACETAL DERIVATIVE; ALCOHOL; BETA HYDROXYCYCLOPENTANONE; CYCLOPENTANONE DERIVATIVE; CYCLOPENTENE DERIVATIVE; ORGANOBORON DERIVATIVE; PYRIDINIUM DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ALKALINITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; DISSOLUTION; PHOTODEGRADATION; PHOTOREACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033531976     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00263-X     Document Type: Article

References (18)

1. (a) Wender PA, Siggel L, Nuss JM. Organic Photochemistry. Editor; Padwa A. New York: Marcel-Dekker, 1989; Vol. 10, Chapter 4.
2. (b) Cornelisse J. Chem. Rev. 1993; 93: 615.
3. (a) Wilzbach KE, Kaplan L, J. Am. Chem. Soc. 1966; 88: 2066.
4. (b) Bryce-Smith D, Gilbert A, Orger BH. J. Chem. Soc., Chem. Commun. 1966: 512.
5. Wender PA. Howbert JJ, J. Am. Chem. Soc. 1981: 103: 688.
6. Wender PA, Dreyer GB, J. Am. Chem. Soc. 1982; 104: 5805.
7. Kaplan L, Pavlik JW, Wilzbach KE. J. Am. Chem. Soc. 1972; 94: 3283.
8. Ling R, Yoshida M, Mariano PS, J. Org. Chem. 1996; 61: 4439.
9. Ling R, Mariano PS, J. Org. Chem. 1998; 63: 6072-6076.
10. Glarner F, Thornton SR, Schärer D, Bernardinelli G, Burger U. Helv. Chim. Acta. 1997; 80: 121.
11. Acar EA, Glarner F, Burger U. Helv. Chim. Acta. 1998; 81: 1095.
12. Corey EJ, Streith J. J. Am. Chem. Soc. 1964; 86: 950.
13. Kohl B, Sturm E, Senn-Bilfinger J, Simon WA, Krüger U, Schaefer H, Rainer G, Figala V, Klemm K. J. Med. Chem. 1992; 35: 1049.
14. Osuch C, Levine R, J. Am. Chem. Soc. 1956; 78: 1723.
15. NOE difference results for compound (13j); (Matrix Presented)
16. Katritzky AR, Wilde H. J. Chem. Soc., Chem. Commun. 1975: 770.
17. The stereochemistry of (15f) has been assigned on the basis of; (a) NOE difference studies (done at 298 K and also at 243 K to freeze out the exchanging OH), (Matrix Presented) (The lack of an NOE enhancement between the Cl-Me and the OH leads us to believe that the stereochemistry is as drawn).
18. (b) and the OH stretching band in the IR spectrum. This remained broad even after dilution indicating a significant degree of intramolecular hydrogen bonding between the hydroxyl group and the aziridinyl nitrogen.