Design of a novel cyclopropane donor bis(trimethylsilylmethyl)cyclopropane and its electron transfer reactions

Chemistry Letters

Volumn , Issue 11, 2001, Pages 1194-1195

  Oku, Akira ^a   Yamauchi, Yoshihito ^a   Schroeder, Marc ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541244     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1194     Document Type: Article

References (21)

1. For example, see a) J. P. Dinnocenzo, H. Zuilhof, D. R. Lieberman, T. R. Simpson, and M. W. McKeckney, J. Am. Chem. Soc., 119, 994 (1997).
2. b) K. Mizuno, N. Ichinose, and Y. Otsuji, J. Org. Chem., 57, 1855 (1992).
3. a) M. Abe and A. Oku, J. Chem. Soc., Chem. Commun., 1994, 1673.
4. b) M. Abe and A. Oku, J. Org. Chem., 60, 3065 (1995).
5. A. Oku, T. Miki, M. Abe, M. Ohira, and T. Kamada, Bull. Chem. Soc. Jpn., 72, 511 (1999).
6. A. Oku, H. Takahashi, and S. M. Asmus, J. Am. Chem. Soc., 122, 7388 (2000).
7. a) K. Mizuno, M. Ikeda, and Y. Otsuji, Tetrahedron Lett., 26, 461 (1985).
8. b) K. Mizuno, M. Ikeda, and Y. Otsuji, Chem. Lett., 1988, 1507.
9. 2-cyclopropane.
10. a) H. E. Simmons, T. L. Cairns, S. A. Valduchick, and C. M. Hoiness, Org. React., 20, 1 (1972).
11. b) S. E. Denmark and J. P. Edwards, J. Org. Chem., 56, 6974 (1991).
12. T. Shioiri, T. Aoyama, and S. Mori, Org. Synth., 68, 1 (1989).
13. Similarly, 3 reacted with TCNE under non-irradiated conditions to afford a five-membered [2+3]cycloadduct. Sequential profile of the reaction was difficult to be proven by the stereochemical analysis of the adduct.
14. Similar types of C-O and C-C bonded intermediates were reported for the reaction of 1 (ref 2b).
15. Review: S. Danishefsky, Acc. Chem. Res., 14, 400 (1981).
16. Formation of complexes between excited carbonyl compounds and Mg salts is reported to retard the back-electron transfer (see refs 2b and 4).
17. (a) C. Pac, A. Nakasone, and H. Sakurai, J. Am. Chem. Soc.,99, 5806 (1977).
18. (b) C. Pac and H. Sakurai, Yuki Gosei Kagaku Kyokaishi, 41, 667 (1983).
19. Among aromatic hydrocarbons examined, pyrene was most effective in comparison with phenanthrene and anthracene.
20. High dilution was effective in the PET reaction of 2 with ketones (ref 3).
21. Gaussian 98, Revision A.5, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.