Alkylidenation of carbonyl compounds with gem-dizincioalkanes mediated with titanium dichloride

Synlett

Volumn , Issue 12, 1998, Pages 1369-1371

  Matsubara, Seijiro ^a   Mizuno, Tsuyoshi ^c   Otake, Tasuyuiki ^c   Kobata, Masami ^c   Utimoto, Kiitiro ^a   Takai, Kazuhiko ^b  

^a KYOTO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000406138     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1980     Document Type: Article

References (26)

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17. 1H NMR of 1 in THF was reported in ref. 9b, but temperature dependence has not been recorded. A broad proton signel (-0.6 - -1.2 ppm) at room temperature, a broad singlet (-1.34 ppm) at -20°C, and a sharp singlet (-1.56 ppm) at -60°C were recorded.
18. Narula, S. P.; Sharma, H. K. Inorg. Syn. 1985, 4. 181.
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20. 1H NMR (300 MHz, 20°C) δ -0.08 (q, J = 7.8 Hz, 1H), 1.45 (d, J = 7.8 Hz, 3H).
21. 1H NMR analysis. The observation indicated that initially produced 2,3-diiodobutane was converted into 2-butene by the action of Zn.
22. Matsubara, S.; Otake, Y.; Morikawa, T.; Utimoto, K. Synlett 1998 1315. The detailed preparation procedure of 14 is described in this paper.
23. (16 Takai, K.; Kataoka, Y.; Okazoe, T.; Utimoto, K. Tetrahedron Lett. 1987, 28, 1443.
24. CH = 118 Hz.
25. The Zn powder from Wako Pure Chemical Industries LTD., Japan, contains 0.04-0.07 mol% of lead based on zinc. Zinc powder was washed with 5% hydrochloric acid according to the following literature: Fieser, L. F.; Fieser, M. In Reagents for Organic Synthesis, Vol 1; Wiley: New York, 1967, p1276.
26. 2