Phenylcyclopropane cation radical revisited: Generation, direct observation and determination of the rates of nucleophilic capture

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1841-1844

  Takahashi, Yasutake ^a   Nishioka, Naoki ^a   Endoh, Fumiyoshi ^a   Ikeda, Hiroshi ^a   Miyashi, Tsutomu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029870135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00157-8     Document Type: Article

References (20)

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9. c) Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc., 1993, 115, 366.
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12. Andre, J. J.; Weil, G. Mol. Phys., 1968, 15, 97; Kobashi, H.; Funabashi, M.; Kondo, T.; Morita, T.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1984, 57, 3557; Kobashi, H.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1986, 59, 1975.
13. Andre, J. J.; Weil, G. Mol. Phys., 1968, 15, 97; Kobashi, H.; Funabashi, M.; Kondo, T.; Morita, T.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1984, 57, 3557; Kobashi, H.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1986, 59, 1975.
14. Andre, J. J.; Weil, G. Mol. Phys., 1968, 15, 97; Kobashi, H.; Funabashi, M.; Kondo, T.; Morita, T.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1984, 57, 3557; Kobashi, H.; Okada, T.; Mataga, N. Bull. Chem. Soc. Jpn., 1986, 59, 1975.
15. -1 at 25°C.
16. +-, 560 nm was used as a monitoring wavelength instead of the apparent maxima, 530 nm.
17. 1c
18. 2) was irradiated by using a 2 kW xenon lamp at 25°C.
19. Conversion was ca. 60%. Formation of 3c and 3d is due to the reaction of intermediate 5 with methanol and t-butanol, respectively.
20. -1, which were significantly higher than our values. Apparently there has been a discrepancy to be resolved. Quite recently, however, we have been informed by Prof. Dinnocenzo that they have remeasured the rates and obtained values more or less close to ours.