1-Chloro-3-trimethylsilylcyclopropene- - A synthesis of 3,3'-bicyclopropenyl

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8717-8720

  Lee, Gon Ann ^a   Chen, Chi Sheng ^a  

^a FU JEN CATHOLIC UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030809935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10317-3     Document Type: Article

References (16)

1. Potgieter, J. H. J. Chem. Ed. 1991, 68, 281.
2. Breslow, R.; Gal, P. J. Am. Chem. Soc. 1959, 81, 4747.
3. Billups, W. E.; Haley, M. M. Angew. Chem. Int. Ed. Engl. 1989, 28, 1711.
4. Billups, W. E.; Haley, M. M. Tetrahedron 1994, 50, 10693.
5. Boese, R.; Bläser, D.; Gleiter, R.; Pfeifer, K.-H.; Billups, W. E.; Haley, M. M. J. Am. Chem. Soc. 1993, 115, 743.
6. Dowd, D.; Gold, A. Tetrahedron Lett. 1969, 85.
7. Lee, G.-A.; Shiau, C.-S.; Chen, C.-S.; Chen, J. J. Org. Chem. 1995, 60, 3565.
8. 3).
9. 3).
10. 2, number of parameters refined 190, final R indiced (obs. data) R = 5.78 %, wR = 6.54 %, goodness-of fit 1.24, data-to-parameter ratio 9.4 : 1, largest difference peak 0.29 eÅ-3, largest difference hole -0.34 eÅ.
11. 3): δ 3.06 (1H, dd, J = 8.4, 3.3 Hz), 2.19 (1H, d, J = 3.4 Hz), 1.30 (1H, dt, J = 8.4, 3.4 Hz), 0.20 (9H, s), 0.08 (9H, s), -0.18 (1H, t, J = 8.4 Hz).
12. Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 829; Hart, D. J.; Hong, W.-P.; Hsu, C-Y. J. Org. Chem. 1987, 52, 4665. For other recent cyclopropene reductions using diimide see: Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492; Billups W. E., Luo, W.; Lee, G.-A.; Chee, J.; Arney, B. E., Jr; Wiberg, K. B.; Arties, D. R. J. Org. Chem. 1996, 61, 764.
13. Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 829; Hart, D. J.; Hong, W.-P.; Hsu, C-Y. J. Org. Chem. 1987, 52, 4665. For other recent cyclopropene reductions using diimide see: Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492; Billups W. E., Luo, W.; Lee, G.-A.; Chee, J.; Arney, B. E., Jr; Wiberg, K. B.; Arties, D. R. J. Org. Chem. 1996, 61, 764.
14. Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 829; Hart, D. J.; Hong, W.-P.; Hsu, C-Y. J. Org. Chem. 1987, 52, 4665. For other recent cyclopropene reductions using diimide see: Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492; Billups W. E., Luo, W.; Lee, G.-A.; Chee, J.; Arney, B. E., Jr; Wiberg, K. B.; Arties, D. R. J. Org. Chem. 1996, 61, 764.
15. Wiberg, N.; Bachhuber, H.; Fischer, G. Angew. Chem. Int. Ed. Engl. 1972, 11, 829; Hart, D. J.; Hong, W.-P.; Hsu, C-Y. J. Org. Chem. 1987, 52, 4665. For other recent cyclopropene reductions using diimide see: Doyle, M. P.; Protopopova, M.; Müller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492; Billups W. E., Luo, W.; Lee, G.-A.; Chee, J.; Arney, B. E., Jr; Wiberg, K. B.; Arties, D. R. J. Org. Chem. 1996, 61, 764.
16. Billups, W. E.; McCord, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1332.