Structure and reactivity of bis(iodozincio)methane in tetrahydrothiophene

Synlett

Volumn , Issue 9, 1999, Pages 1471-1473

  Matsubara, Seijiro ^a   Yamamoto, Yuhei ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

1,3 diketone; Dimetal; EXAFS; THT; Zinc

Indexed keywords

CHLORIDE; DIKETONE; TETRAHYDROTHIOPHENE DERIVATIVE; ZINC;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY;

EID: 0032863117     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2877     Document Type: Article

References (15)

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4. d) Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B.J.J.; Schat, M.A.; Tinga, G.; Akkerman, O.S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
5. d) Bertini, F.; Grasselli, P.; Zubiani, G.; Cainelli, G. Tetrahedron 1970, 26, 1281; van de Heisteeg, B.J.J.; Schat, M.A.; Tinga, G.; Akkerman, O.S.; Bickelhaupt, F. Tetrahedron Lett. 1986, 27, 6123.
6. e) Takai, K.; Kakiuchi, T.; Utimoto, K. J. Org. Chem. 1994, 59, 2671.
7. f) Matsubara, S.; Mizuno,T.; Otake, Y.; Kobara, M.; Utimoto, K.; Takai, K. Synlett 1998, 1369.
8. g) Utimoto, K.; Toda, N.; Mizuno, T.; Kobata, M.; Matsubara, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2804.
9. h) Matsubara, S.; Otake, Y.; Morikawa, T.; Utimoto, K. Synlett 1998, 1315.
10. Matsubara, S.; Kawamoto, K.; Utimoto, K. Synlett 1998, 267.
11. Zinc(II) halide containing the reagent may assists the ring opening of THF as Lewis acid. In reference 2, the preparation of 1,3-diketone in the presence of Pd catalyst is shown.
12. 2, and Zn in THT did not afford 1. Other solvents, such as ether, DME, and 1,4-dioxane were also examined as a solvent for the preparation of 1. Only the reaction in 1,4-dioxane afforded 1 in 8% yield, and the reactoins in ether and DME did not give 1.
13. 1H nmr of reagent did not show the signal from the proton based on THF.
14. A Structural study of organozincate by EXAFS: Uchiyama, M.; Kameda, M.; Mishima, O.; Yokoyama, N.; Koike, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc., 1998, 120, 4943.
15. 2 in a momomeric form.