Photocyclization of cinnamylnaphthols

Tetrahedron

Volumn 54, Issue 17, 1998, Pages 4337-4344

  Jiménez, M Consuelo ^a   Leal, Pablo ^a   Miranda, Miguel A ^a   Scaiano, Juan C ^b   Tormos, Rosa ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHOL DERIVATIVE;

ARTICLE; CYCLIZATION; ENERGY TRANSFER; FLUORESCENCE; ISOMERISM; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032560153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00147-1     Document Type: Article

References (16)

1. 1. Horspool, W. M.; Pauson, P. L. J. Chem. Soc., Chem. Commun. 1967, 195-196.
2. 2. Fréter, G.; Schmid, H. Helv. Chim. Acta 1967, 50, 255-262.
3. 3. Kropp, P. J.; Krauss, H. J. J. Am. Chem. Soc. 1969, 91, 7466-7474.
4. 4. Shani, A.; Mechoulam, R. Tetrahedron 1971, 27, 601-606.
5. 5. Houri, S.; Geresh, S.; Shani, A. Isr. J. Chem. 1973, 11, 805-818.
6. 6. Geresh, S.; Levy, O.; Markovits, Y.; Shani, A. Tetrahedron 1975, 31, 2803-2807.
7. 7. Kitamura, T.; Imagawa, T.; Kawanisi, M. Tetrahedron 1978, 34, 3451-3457.
8. 8. Chow, Y. L.; Zhou, X.-M.; Gaitan, T. J.; Wu, Z.-Z. J. Am. Chem. Soc. 1989, 111, 3813-3818.
9. 9. Morrison, H. Org. Photochem. 1979, 4, 143-188.
10. 10. Jiménez, M. C.; Márquez, F.; Miranda, M. A.; Tormos, R. J. Org. Chem. 1994, 59, 197-202.
11. 11. Jiménez, M. C.; Miranda, M. A.; Tormos, R. Tetrahedron. 1997, 53, 14729-14736.
12. nd Edition; Marcel Dekker Inc.: New York, 1993, pp 33 and 47.
13. +, 28), 169 (100), 168 (55), 141 (53), 139 (16), 128 (19), 117 (17), 115 (27), 91 (44), 77 (12).
14. 14. Photocyclization of 1e could be partially occurring via electron transfer, which has also been proposed as a possible mechanism for this type of reaction (see Ref 9). It is worth mentioning that the oxidation potential of 1-naphthol is sligthly lower (0.1 V) than that of 2-naphthol: Weinberg, N. L. Techniques of Etectroorganic Synthesis Part II. In Techniques of Chemistry Vol. V; John Wiley & Sons: New York 1975, p. 740.
15. ......π bonds in the photochemical behaviour of o-ethylenic phenols and anilines is discussed in: Trinquier, G.; Malrieu, J.-P. J. Mol. Struct. 1978, 49, 155-170.
16. a*values are 1.8 (for 1e) and 2.4 (for 1f).