Determination of the photolytic decomposition pathways of benzylchlorodiazirine by C60 probe technique

Tetrahedron Letters

Volumn 48, Issue 5, 2007, Pages 859-861

  Ishitsuka, Midori O ^a   Enoki, Haruka ^a   Nikawa, Hidefumi ^a   Wakahara, Takatsugu ^a   Tsuchiya, Takahiro ^a   Akasaka, Takeshi ^a   Liu, Michael T H ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b UNIVERSITY OF PRINCE EDWARD ISLAND   (Canada)

Author keywords

C60; Carbene; Diazirine; Photolytic decomposition; RIES process

Indexed keywords

AZIRINE DERIVATIVE; BENZYLCHLORODIAZIRINE; CARBENE; CARBON; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DECOMPOSITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR PROBE; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 33845894701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.145     Document Type: Article

References (20)

1. Richards F.M., Lamed R., and Wynn R. Protein Sci. 9 (2000) 2506-2517
2. Korshunova G.A., Sumbatyan N.V., and Topin A.N. Mol. Biol. 34 (2000) 823
3. In: Liu M.T.H. (Ed). Chemistry of Diazirines Vols. 1 and 2 (1987), CRC Press, Boca Raton, Florida
4. Frey H.M., and Stevens I.D.R. J. Chem. Soc. (1965) 1700
5. Modarelli D.A., Morgan S., and Platz M.S. J. Am. Chem. Soc. 114 (1992) 7034
6. Tomioka H., Hayashi N., Izawa Y., and Liu M.T.H. J. Am. Chem. Soc. 106 (1984) 454-456
7. Liu M.T.H. J. Chem. Soc., Chem. Commun. (1985) 982-984
8. Liu M.T.H., and Bonneau R. J. Am. Chem. Soc. 112 (1990) 3915-3919
9. Nigam M., Platz M.S., Showalter B.M., Toscano J.P., Johnson R., Abbot S.C., and Kirchhoff M.M. J. Am. Chem. Soc. 120 (1998) 8055-8059
10. Akasaka T., Liu M.T.H., Niino Y., Maeda Y., Wakahara T., Okamura M., Kobayashi K., and Nagase S. J. Am. Chem. Soc. 122 (2000) 7134-7135
11. Wakahara T., Niino Y., Kato T., Maeda Y., Akasaka T., Liu M.T.H., Kobayashi K., and Nagase S. J. Am. Chem. Soc. 124 (2002) 9465-9468
12. Liu M.T.H., Choe Y.-K., Kimura M., Kobayashi K., Nagase S., Wakahara T., Niino Y., Ishitsuka M.O., Maeda Y., and Akasaka T. J. Org. Chem. 68 (2003) 7471-7478
13. Ishitsuka M.O., Niino Y., Wakahara T., Akasaka T., Liu M.T.H., Kobayashi K., and Nagase S. Tetrahedron Lett. 45 (2004) 6321-6322
14. Graham W.H. J. Am. Chem. Soc. 87 (1965) 4396-4397
15. 3 (4/1)) δ 39.15 (t, 1C), 57.42 (s, 1C), 78.86 (s, 2C), 127.48 (d, 1C), 128.62 (d, 2C), 129.96 (d, 2C), 135.44 (s, 1C), 137.22 (s, 2C), 138.85 (s, 2C), 140.76 (s, 2C), 141.04 (s, 2C), 141.62 (s, 2C), 141.90 (s, 2C), 141.96 (s, 2C), 142.10 (s, 2C), 142.66 (s, 1C), 142.75 (s, 1C), 142.80 (s, 2C), 142.84 (s, 2C × 2), 143.08 (s, 2C), 143.39 (s, 2C), 143.48 (s, 2C), 144.20 (s, 2C), 144.27 (s, 1C), 144.31 (s, 2C), 144.32 (s, 2C), 144.38 (s, 2C, 1C), 144.60 (s, 2C), 144.75 (s, 2C × 2), 144.87 (s, 2C), 144.94 (s, 2C), 144.98 (s, 2C × 2), 145.53 (s, 2C), 145.83 (s, 2C).
16. Hirsch A., Grösser T., Skiebe A., and Soi A. Chem. Ber. 126 (1993) 1061-1067
17. -3, respectively. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 622039. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
18. 6; scan rate: 50 mV/s; working electrode: Pt disc; counter electrode: Pt wire; reference electrode: SCE.
19. Liu M.T.H., and Bonneau R. J. Am. Chem. Soc. 114 (1992) 3604-3607
20. Akasaka T., Maeda Y., Wakahara T., Okamura M., Fujitsuka M., Ito O., Kobayashi K., Nagase S., Kako M., Nakadaira Y., and Horn E. Org. Lett. (1999) 1509-1512