Living coordination polymerization of alkylallenes by π-allylnickel catalyst: Observation of an extremely high polymerizability of 1,2-cyclononadiene

Chemistry Letters

Volumn , Issue 11, 1997, Pages 1187-1188

  Takagi, Koji ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006310151     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1187     Document Type: Article

References (18)

1. For the recent review, see, for example: (a) M. Sawamoto Petrotech (Tokyo), 19, 814 (1996).
2. (b) T. Aida Petrotech (Tokyo), 19, 811 (1996).
3. (c) T. Endo and I. Tomita Macromol. Symp., 84, 73 (1994).
4. (d) M. M. Green Chemtracts: Macromol. Chem., 3, 326 (1992).
5. (e) R. H. Grubbs and W. Tumas Science, 243, 907 (1989).
6. (a) I. Tomita, Y. Kondo, K. Takagi, and T. Endo Macromolecules, 27, 4413 (1994).
7. (b) I. Tomita, Y. Kondo, K. Takagi, and T. Endo Acta Polymerica, 46, 432 (1995).
8. (a) K. Takagi, I. Tomita, and T. Endo Macromolecules, submitted.
9. (b) I. Tomita, Y. Kondo, K. Takagi, and T. Endo Polym. Prepr. Jpn., 44, 1296 (1995).
10. K. Takagi, I. Tomita, and T. Endo, Tetrahedron, in press.
11. 3 (3 ml). By the precipitation in MeOH (100 ml), poly(2a) was obtained in 96% yield (0.094 g).
12. 1H NMR spectrum, the double bond on the polymer backbone was observed quantitatively by comparing the integral ratio of the double bond peak with aliphatic ones.
13. -1) 2930, 2857, 1638, 1462, 1446, 1265.
14. 0=1.0 M,) was performed in toluene containing n-tetradecane (0.038 M) as an internal standard at 0°C similarly to the above mentioned procedure. After the designated reaction period at 0°C, a small portion of the reaction mixture was sampled by the syringe (ca. 10 μl) and the conversion of the monomer was estimated by the GC analyses.
15. -1, respectively, although the value for 2a may include a substantial error.
16. W. R. Moore and H. R. Ward, J. Org. Chem., 27, 4179 (1962).
17. According to the calculation of the strain energies of 2a, see, A. L. A. Frank and Y. Issa J. Am. Chem. Soc., 99, 7640 (1977). In the addition reaction of hydrogen bromide to cyclic allenes, more strained cyclic allene has been reported to afford a HBr adduct in higher yield (86 % from 2a, 75 % from 1,2-cyclodecadiene, and 70 % from 2b). See, S. N. Moorthy, A. Singh, D. Devaprabhakara J. Org. Chem., 40, 3452 (1975).
18. According to the calculation of the strain energies of 2a, see, A. L. A. Frank and Y. Issa J. Am. Chem. Soc., 99, 7640 (1977). In the addition reaction of hydrogen bromide to cyclic allenes, more strained cyclic allene has been reported to afford a HBr adduct in higher yield (86 % from 2a, 75 % from 1,2-cyclodecadiene, and 70 % from 2b). See, S. N. Moorthy, A. Singh, D. Devaprabhakara J. Org. Chem., 40, 3452 (1975).