Some single electron-transfer reactions of arylimines

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1997, Pages 2337-2343

  Brown, David W ^a   Lindquist, Monika ^b   Mahon, Mary F ^a   Malm, Bengt ^b   Nilsson, Göran N ^b   Ninan, Aleyamma ^a   Sainsbury, Malcolm ^a   Westerlund, Christer ^b  

^a UNIVERSITY OF BATH   (United Kingdom)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748648672     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701947e     Document Type: Article

References (20)

1. We first encountered the dimers 7 and the 2-hydroxybenzoxazine 6 (R = H) as by-products (yields 10 and 3%, respectively) formed by the oxidation of the imine 3 (X = 2H) during work-up (see Experimental section).
2. H. Gilman, J. E. Kirby and C. R. Kinney, J. Am. Chem. Soc., 1929, 51, 2252. In Gilman's experiment the imine and the Grignard reagent were heated together in diethyl ether and toluene for 6 h.
3. R. C. Fuson and D. C. McKusick, J. Am. Chem. Soc., 1945, 67, 597.
4. A SET mechanism for the reaction of Grignard reagents and imines was proposed by M. Okubo and S. Ueda (Bull. Chem. Soc., Jpn., 1979, 52, 3346).
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9. B. J. Wakefield, in Organolithium Methods, Academic Press, New York, 1988;
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11. W. F. Bailey, FMC Lithium Link, Spring 1995;
12. W. F. Bailey, J. J. Patricia, T. T. Nurmi and W. Wang, Tetrahedron Lett., 1986, 27, 1861;
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14. W. F. Bailey and J. J. Patricia, J. Organomet. Chem., 1988, 342, 1.
15. Comounds 8, 15 (R = H) and 15 (R = Bu′) were kindly provided by Astra Hässle AB.
16. Although this is shown as a two electron process, it could equally be a radical mediated rearrangement.
17. Although we only observed one diastereoisomer from the cycloaddition, many recrystallizations were carried out before a suitable crystal for the X-ray analysis was obtained. Thus, it is possible that we selected out one of two possible racemic adducts differing only in the relative configurations of the hydroxy and tert-butyl groups.
18. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.
19. G. M. Sheldrick, SHELXL-93, a computer program for crystal structure refinement, University of Göttingen, Germany. 1993.
20. P. McArdle, J. Appl. Cryst., 1994, 27, 438.