An efficient synthesis of α-(trimethylselyl)allenyl ketones

Synthetic Communications

Volumn 26, Issue 4, 1996, Pages 803-807

  Cunico, Robert F ^a   Nair, Sajiv K ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030029851     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608086756     Document Type: Article

References (14)

1. Cunico, R.F. Tetrahedron Lett. 1994, 35, 2291.
2. (a) Reich, H.J.; Olson, R.E.; Clarck, M.C. J. Am. Chem. Soc. 1980, 102, 1423.
3. (b) Kuwajima, I.; Kato, M. Tetrahedron Lett. 1980, 21, 623.
4. For similar examples producing [3]cumulenes from alkoxide expulsion, see (a) Ref, 2b and (b) Bienz, S.; Enev, V.; Huber, P. Tetrahedron Lett., 1994, 35, 1161.
5. For similar examples producing [3]cumulenes from alkoxide expulsion, see (a) Ref, 2b and (b) Bienz, S.; Enev, V.; Huber, P. Tetrahedron Lett., 1994, 35, 1161.
6. -1; 1H NMR: 4.45, 4.42 (AB pattern, J = 9.2 Hz, 2H), 2.01 (s, 3H), 0.23 (s, 9H). These parallel values previously reported (ref 3b) for similar (air-unstable) [3]cumulenyloxysilanes.
7. 1H NMR analysis of the crude reaction product.
8. Comparative yields were calculated starting with the 3-trimethylsiloxy-1-alkyne or from ethynylmagnesium bromide and acetyltrimethylsilane as employed in ref. 1.
9. 1a, 1c: Aldrich Chemical Co., Milwaukee, Wisconsin. 1b: Brandsma, L.; Verkruijsse, H.D. Synthesis of Acetylenes, Allenes and Cumulenes 1981, Elsevier, Amsterdam, p. 217. 1d: Bartmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515. 1e: Obtained in low yield by the method of Rahimizadeh, M.; Waight, E.S. J. Chem. Res. (M) 1978, 2340.
10. 1a, 1c: Aldrich Chemical Co., Milwaukee, Wisconsin. 1b: Brandsma, L.; Verkruijsse, H.D. Synthesis of Acetylenes, Allenes and Cumulenes 1981, Elsevier, Amsterdam, p. 217. 1d: Bartmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515. 1e: Obtained in low yield by the method of Rahimizadeh, M.; Waight, E.S. J. Chem. Res. (M) 1978, 2340.
11. 1a, 1c: Aldrich Chemical Co., Milwaukee, Wisconsin. 1b: Brandsma, L.; Verkruijsse, H.D. Synthesis of Acetylenes, Allenes and Cumulenes 1981, Elsevier, Amsterdam, p. 217. 1d: Bartmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515. 1e: Obtained in low yield by the method of Rahimizadeh, M.; Waight, E.S. J. Chem. Res. (M) 1978, 2340.
12. No product was obtained when THF was used as solvent.
13. Cunico, R.F.; Kuan, C.-P. J. Org. Chem. 1985, 50, 5410.
14. 2 18h, evacuation at 80°C (1 mm), dissolution in anhydrous ether and filtration through a 0.2 μm PTFE syringe filter.