1,4-Silylstannation of 1,3-Dienes Catalyzed by Platinum Complex

Journal of the American Chemical Society

Volumn 113, Issue 24, 1991, Pages 9368-9369

  Tsuji, Yasushi ^a   Obora, Yasushi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000893923     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00024a052     Document Type: Article

References (31)

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20. A typical procedure is as follows: 1,3-Butadiene (1.5 mmol, 0.94 mL of 1.6 M stock solution in toluene), Pt(CO)2(PPh3)2 (19 mg, 0.025 mmol), la (181 mg, 0.5 mmol), toluene (2.0 mL), and a magnetic stirring bar were placed under argon flow in a 30 mL stainless steel autoclave containing an inserted glass tube. An air purge was confirmed by three pressurization (20 atm)-depressurization sequences with argon. After the reaction, the mixture was passed through a short Florisil column (8 mm i.d. × 50 mm) and the product (3a) was isolated by Kugelrohr distillation (pot temperature 115 °C (0.5 mmHg); 175 mg, 84%).
21. 3a: 1H NMR (CDC13) δ −0.02 (s, 9 H), 0.82−0.94 (m, 15 H), 1.24−1.55 (m, 12 H), 1.48 (d, 2 H), 1.70 (d, 2 H, 2JSn−H = 58 Hz), 5.19 (dt, 1 H,y= 15 Hz, 7 Hz), 5.38 (dt, 1 H,J= 15 Hz, 7 Hz); l3C NMR (CDC13) δ −1.87 (q), 9.15 (t, 1JSn−c = 296 Hz, 310 Hz), 13.74 (q), 14.26 (t), 22.61 (t, 1JSn−c = 261, 270 Hz), 27.42 (t, 2JSn−c = 65 Hz), 29.26 (t, 3JSn−c = 24 Hz), 121.5 (d, JSn−c = 48 Hz), 127.6 (d, JSn−c = 44 Hz); I19Sn NMR (C6D6) −17.74 ppm;MS(EI) m/e418(M+). Anal. Found: C, 54.40; H, 10.08. Calcd for C19H42SnSi: C, 54.68; H, 10.14. 3b: 1H NMR (CDCI3) δ −0.01 (s, 9 H), 0.83−0.96 (m, 15 H), 1.24−1.56 (m, 12 H), 1.50 (d, 2 H), 1.55 (s, 3 H), 1.77 (s, 2 H, 2Jsn−H = 59 Hz11), 5.03 (t, 1 H); 13C NMR (CDC13) δ −1.57 (q), 9.54 (t, 1Jsn−C = 292, 306 Hz), 13.77 (q), 18.46 (q), 18.73 (t), 22.25 (t, 1Jsn−C = 261, 271 Hz), 27.55 (t, 2Jsn−C = 54 Hz), 29.32 (t, 3Jsn−C = 24 Hz), 115.9 (d, 1Jsn−C = 44 Hz), 132.3 (s, 2Jsn−C = 44 Hz); 119Sn NMR −16.04 ppm; MS (EI) m/e 432 (M+). Anal. Found: C, 55.40; H, 10.52. Calcd for C20H44SnSi: C, 55.69; H, 10.28.
22. Only one side (lower field) of the satellite peaks was observed. The pair (higher field) to the observed side could not be distinguished because of overlap with other proton resonances.
23. Other selected transition-metal catalyst precursors (5 mol %) such as RhCl(PPh3)3, IrCl(CO)(PPh3)2, Ru(COD)(COT), and Mn2(CO),0 did not give any 1,4-silylstannation products at all.
24. The reaction of l4 or disilanes14 with alkynes affords only (Z)-alkenes stereoselectively. 1,4-Disilylation of 1,3-dienes with disilanes15 also gave (Z)-l,4-disilyl products. In the present 1,4-silylstannation reaction, there might be some possibility that (Z)-l,4 adducts are kinetic products and the (E)-l,4 products are formed via (Z)-(E) isomerization. However, any (Z)-l,4 adducts were not detected in the reaction mixtures even at lower conversions of 1, indicating that such (Z)-(E) isomerization during the course of the reaction is unlikely.
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