A four-member ring hypervalent iodine radical

Journal of Physical Chemistry A

Volumn 102, Issue 48, 1998, Pages 9975-9977

  Miranda, Miguel A ^a   Pérez Prieto, Julia ^b   Font Sanchis, Enrique ^a   Kónya, Klára ^c   Scaiano, J C ^c  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000325018     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp982103y     Document Type: Article

References (21)

1. Cristol, S. J.; Bindel, T. H. J. Org. Chem. 1980, 45, 951. Meisel, D.; Das, P. K.; Hug, G. L.; Bhattacharyya, K.; Fessenden, R. W. J. Am. Chem. Soc. 1986, 108, 4706. Tokumura, K.; Udogawa, M.; Otaki, T.; Itoh, M. Chem. Phys. Lett. 1987, 141, 558.
2. Cristol, S. J.; Bindel, T. H. J. Org. Chem. 1980, 45, 951. Meisel, D.; Das, P. K.; Hug, G. L.; Bhattacharyya, K.; Fessenden, R. W. J. Am. Chem. Soc. 1986, 108, 4706. Tokumura, K.; Udogawa, M.; Otaki, T.; Itoh, M. Chem. Phys. Lett. 1987, 141, 558.
3. Cristol, S. J.; Bindel, T. H. J. Org. Chem. 1980, 45, 951. Meisel, D.; Das, P. K.; Hug, G. L.; Bhattacharyya, K.; Fessenden, R. W. J. Am. Chem. Soc. 1986, 108, 4706. Tokumura, K.; Udogawa, M.; Otaki, T.; Itoh, M. Chem. Phys. Lett. 1987, 141, 558.
4. Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592; Pérez-Prieto, J.; Miranda, M. A.; Garcia, H.; Koǹya, K.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773.
5. Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592; Pérez-Prieto, J.; Miranda, M. A.; Garcia, H.; Koǹya, K.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773.
6. Zhang, B.; Pandit, C. R.; McGimpsey, W. G. J. Phys. Chem. 1994, 98, 7022.
7. Banks, J. T.; Garcia, H.; Miranda, M. A.; Pérez-Prieto, J.; Scaiano, J. C. J. Am. Chem. Soc. 1995, 117, 5049.
8. Ouchi, A.; Yabe, A.; Adam, W. Tetrahedron Lett. 1994, 35, 6309. Ouchi, A.; Koga, Y. J. Org. Chem. 1997, 62, 7376.
9. Ouchi, A.; Yabe, A.; Adam, W. Tetrahedron Lett. 1994, 35, 6309. Ouchi, A.; Koga, Y. J. Org. Chem. 1997, 62, 7376.
10. Scaiano, J. C. J. Am. Chem. Soc. 1980, 102, 7747.
11. Scaiano, J. C.; Tanner, H.; Weir, D. J. Am. Chem. Soc. 1985, 107, 4396.
12. Banks, J. T.; Scaiano, J. C.; Adam, W.; Schulte-Oestrich, R. J. Am. Chem. Soc. 1993, 115, 2473.
13. Under similar conditions, 1,3-diphenyl-1-iodopropane was converted into a mixture of trans-1,3-diphenylpropene (53%) and 1,3-diphenylpropane (47%), through disproportionation of the 1,3-diphenyl-1-propyl radical intermediate. Thus, the intermediacy of the monoiodo compound in the photolysis of 1 can be safely ruled out since 1,3-diphenylpropane was not observed in its photolysate.
14. Irradiation of trans-5 under similar conditions led to its isomerization to the cis-isomer (67%). By contrast, when iodine was added to the solution before the irradiation, no transformation was detected. This suggests quenching of the excited olefin by the iodine.
15. Shoute, L. C. T.; Neta, P. J. Phys. Chem. 1991, 95, 4411.
16. •- radical shows a maximum at 390 nm, i.e., at the correct wavelength to contribute to this absorption. However, the complex with the starting material is a more likely candidate in nonpolar cydohexane: Hug, G. L. Optical Spectra of Nonmetallic Inorganic Transient Species in Aqueous Solution; National Bureau of Standards: Washington, 1981; NSRDS-NBS 69, p 54. Attempts to monitor the iodine-benzene complex by performing the experiment in benzene with 308 nm excitation were only partially satisfactory; a growth in the signal at 490 nm was detected, but determining this was somewhat complicated by the fact that this wavelength required higher concentrations of precursor 1, which also forms a complex with iodine atoms (see ref 11).
17. Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kònya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923. Miranda, M. A.; Pérez-Prieto, J.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. J. Org. Chem. 1997, 62, 5713.
18. Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kònya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923. Miranda, M. A.; Pérez-Prieto, J.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. J. Org. Chem. 1997, 62, 5713.
19. Chatgilialoglu, C. In Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, 1989, Vol. 2, p 3.
20. High-intensity photolysis studies of dihalides have also been carried out by means of the laser-jet technique: Adam. W.; Ouchi, A. Tetrahedron Lett. 1992, 33, 1875.
21. Griffin, G. W.; Covell, J.; Petterson, R. C.; Dodson, R. M.; Klose, G. J. Am. Chem. Soc. 1965, 87, 1410.