Cyclopropanation by tandem radical [2 + 1] cycloaddition conducted by nickel complexes catalyzed electroreduction

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2705-2708

  Ozaki, Shigeko ^a   Matsui, Eiki ^a   Waku, Junya ^a   Ohmori, Hidenobu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031003930     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00434-6     Document Type: Article

References (43)

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23. -1 at 60 ° C. For detail, see ref. 9a.
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32. For synthesis of 1 see: Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093; Ando, T.; Yamawaki, J.; Kawata, T.; Sumi, S.; Hanafusa, T.; Bull. Chem. Soc. Jpn. 1982, 55, 2504-2507; Parsons, J. P.; Caddick, S. Tetrahedron, 1994, 50, 13523-13532; Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Tetrahedron Lett., 1986, 27, 4763-4766. The vinyl bromides 1 (e, f, and g) exhibit reductive peak potentials at around -2.2 V. vs. SCE, while the simple vinyl bromides exhibit those at around -2.8 V vs. SCE.
33. For synthesis of 1 see: Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093; Ando, T.; Yamawaki, J.; Kawata, T.; Sumi, S.; Hanafusa, T.; Bull. Chem. Soc. Jpn. 1982, 55, 2504-2507; Parsons, J. P.; Caddick, S. Tetrahedron, 1994, 50, 13523-13532; Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Tetrahedron Lett., 1986, 27, 4763-4766. The vinyl bromides 1 (e, f, and g) exhibit reductive peak potentials at around -2.2 V. vs. SCE, while the simple vinyl bromides exhibit those at around -2.8 V vs. SCE.
34. For synthesis of 1 see: Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093; Ando, T.; Yamawaki, J.; Kawata, T.; Sumi, S.; Hanafusa, T.; Bull. Chem. Soc. Jpn. 1982, 55, 2504-2507; Parsons, J. P.; Caddick, S. Tetrahedron, 1994, 50, 13523-13532; Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Tetrahedron Lett., 1986, 27, 4763-4766. The vinyl bromides 1 (e, f, and g) exhibit reductive peak potentials at around -2.2 V. vs. SCE, while the simple vinyl bromides exhibit those at around -2.8 V vs. SCE.
35. For synthesis of 1 see: Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093; Ando, T.; Yamawaki, J.; Kawata, T.; Sumi, S.; Hanafusa, T.; Bull. Chem. Soc. Jpn. 1982, 55, 2504-2507; Parsons, J. P.; Caddick, S. Tetrahedron, 1994, 50, 13523-13532; Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Tetrahedron Lett., 1986, 27, 4763-4766. The vinyl bromides 1 (e, f, and g) exhibit reductive peak potentials at around -2.2 V. vs. SCE, while the simple vinyl bromides exhibit those at around -2.8 V vs. SCE.
36. We have indicated that the radicals stabilized by elctron-withdrawing groups at a position are more reducible than smiple alkyl radicals and so they are reduced at the reductive potential of Ni(II) to the corresponding carbanions which would be read with water which is present in DMF or DMSO as a contaminant at the rate that is expected to be much greater than those of hydrogen abstraction from the solvents by the stabilized radicals
37. In electrolysis in a divided cell, a graphite plate and a platinum foil were used as a cathode and an anode, respectively. In electrolysis in an undivided cell a graphite plate and a zinc plate were used as a cathode and a sacrificial anode, respectively. Tetraethylammonium perchlorate (TEAP) (1 mmol) was used as a supporting electrolyte. Electricity of 2F/mol based on the halides was passed galvanoslatically ( 3 mA). Complexes A and B are shown below.) (Formula presented)
38. 2CH, cyclopropyl). The stereochemical assignments of 2h were based on the NOE experiments. (Formula presented)
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42. 17
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