A novel synthesis of spirocyclopropenes from the haloallene derivatives with alkanethiolate ions

Chemistry Letters

Volumn , Issue 1, 1997, Pages 21-22

  Toda, Takashi ^a   Kuwana, Masahiro ^a   Ohhashi, Yoshitaka ^a   Yoshida, Masaaki ^a  

^a UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031509466     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.21     Document Type: Article

References (11)

1. H. E. Simmons and T. Fukunaga, J. Am. Chem. Soc., 89, 5208 (1967).
2. H. Durr and R. Gleiter, Angew. Chem., Int. Ed. Engl., 17, 559 (1978).
3. W. E. Billups, W. Luo, and M. Gutierrez, J. Am. Chem. Soc., 116, 6463 (1994).
4. H. Durr, Angew. Chem., Int. Ed. Engl., 28, 413 (1989).
5. H. Durr, Y. Ma, and G. Cortellaro, Synthesis, 1995, 294.
6. T. Toda, N. Shimazaki, H. Hotta, T. Hatakeyama, and T. Mukai, Chem. Lett., 1978, 523.
7. M. Minabe, M. Yoshida, S. Saito, K. Tobita, and T. Toda, Bull. Chem. Soc. Jpn., 61, 2067 (1988).
8. 22S: C, 82.30; H, 7.24%.
9. 3) δ -0.92, -0.25, 53.93 (C-9), 87.26 (TMS-C≡), 105.20, 111.40 (TMS-C=), 119.97, 120.04, 122.08, 125.51, 126.70, 126.89, 128.07, 128.45, 137.81, 138.67, 140,23, 147.17, 204.90 (=C=).
10. The reaction with amines gave complicated mixture, while with alcohols it afforded 9-alkoxy-9-ethynylfluorene derivatives in good yields.
11. Z. Rappoport, Acc. Chem. Res., 25, 474 (1992).