(tert-butyldimethylsilyl)allene: [ Silane, (1,1-dimethylethyl)dimethyl-1,2-propadienyl- ]

Organic Syntheses

Volumn 76, Issue , 1999, Pages 178-

  Myers, Andrew G ^b   Zheng, Bin ^a   Matsunaga, Kazuya ^b   Danheiser, Rick L ^b  

^a California Institute of Technology ^*  (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026923637     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.076.0178     Document Type: Article

References (13)

1. Jones, R. G.; Mann, M. J. J. Am. Chem. Soc. 1953, 75, 4048.
2. Duhamel, L.; Plaquevent, J.-C. J. Org. Chem. 1979, 44, 3404.
3. Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407. In this paper, 3-(tert-butyldimethylsilyl)-2-propyn-1-ol was prepared in one step (76% yield, 95% purity) by treatment of propargyl alcohol with 2.1 equiv of EtMgBr and 1.0 equiv of TBDMSCl in THF at reflux for 8 days.
4. Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507.
5. Levek, T. J.; Kiefer, E. F. J. Am. Chem. Soc. 1976, 98, 1875.
6. Reviews: (a) Rossi, R.; Diversi, P. Synthesis 1973, 25;
7. "The Chemistry of Ketenes, Allenes, and Related Compounds"; Patai, S., Ed.; Wiley: New York, 1980;
8. "The Chemistry of the Allenes"; Landor, S. R., Ed.; Academic Press: London, 1982;
9. "Allenes in Organic Synthesis"; Schuster, H. F.; Coppola, G. M., Ed.; Wiley: New York, 1984;
10. Pasto, D. J. Tetrahedron 1984, 40, 2805.
11. Danheiser, R. L.; Tsai, Y.-M.; Fink, D. M. Org. Synth., Coll. Vol. VIII 1993, 471;
12. Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935.
13. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.