Initiation of tin-mediated radical reactions by diethylzinc-air

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6335-6336

  Ryu, Ilhyong ^a   Araki, Fumikazu ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMANTADINE; BENZOFURAN DERIVATIVE; FREE RADICAL; OXYGEN;

ARTICLE; AUTOOXIDATION; CHEMICAL REACTION; OXIDATION; POLYMERIZATION; STEADY STATE;

EID: 0032572888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01345-8     Document Type: Article

References (20)

1. 1. a) Curran, D. P.; Porter, N. A.; Giese, B. Stereoselectivity of Radical Reactions; VCH: Weinheim, 1995.
2. b) Smadja, W. Synlett 1994, 1-26.
3. c) Guindon, Y.; Jung, G.; Guérin, B.; Ogilvie, W. W. Synlett 1998, 213-220.
4. 2. a) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547-2539.
5. b) Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3465-3467.
6. 3. Initiation by sonication or electrolysis, see: a) Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178-8786.
7. b) Tanaka, H.; Ogawa, H.; Suga, H.; Torii, S. J. Org. Chem. 1996, 61, 9402-9408.
8. 4. a) Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83-134.
9. b) Sakata, R.; Tsuruta, T.; Saegusa, T.; Furukawa, J. Kogyo Kagaku Zasshi 1960, 63, 1817-1822.
10. c) Lal, J. J. Polym. Sci., Part A-1 1966, 4, 1163-1177.
11. d) Miyano, S.; Yamashita, J.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1972, 45, 1946.
12. e) Rousseau, G.; Slougui, N. J. Am. Chem. Soc. 1984, 106, 7283-7285.
13. 2 (Aldrich) was used for this study.
14. 2-air gave a 82/18 ratio.
15. 7. For aerobic radical reaction mediated by tin hydride leading to alcohols, see: Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1987, 113, 8980-8982.
16. 2, see: a) Abraham, M. H. J. Chem. Soc. 1960, 4130-4135.
17. b) Yamamoto, K.; Yamamoto, N. Chem. Lett. 1989, 1149-1152.
18. c) Enders, D.; Zhu, J.; Raabe, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1725-1728.
19. d) Sosnovsky, G.; Brown, J. H. Chem. Rev. 1966, 66, 529-566.
20. e) Davies, A. G.; Roberts, B. P. J. Chem. Soc., B 1968, 1074-1078.