Sequential carbometalation/elimination reaction takes place between gallium enolate and chloroethyne

Chemistry Letters

Volumn 32, Issue 3, 2003, Pages 298-299

  Amemiya, Ryo ^a   Fujii, Akiko ^a   Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; CARBON; CHEMICAL COMPOUND; CHLOROETHYNE; CHLOROTRIMETHYLSILYLETHYNE; GALLIUM ENOLATE; KETONE DERIVATIVE; SILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; CARBOMETALLATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; ELIMINATION REACTION; ENDIYNYLLATION; ENTRIYNYLATION; ETHYNYLATION;

EID: 0037790859     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.298     Document Type: Article

References (7)

1. 3: K. Kobayashi, M. Arisawa, and M. Yamaguchi, J. Am. Chem. Soc., 124, 8528 (2002).
2. 3: K. Kobayashi, M. Arisawa, and M. Yamaguchi, J. Am. Chem. Soc., 124, 8528 (2002).
3. M. Yamaguchi, A. Hayashi, and M. Hirama, Chem. Lett., 1995, 1093.
4. K. Okuhara, J. Org. Chem., 41, 1487 (1976).
5. Sequential carbometalation reaction of organocopper reagent with acetylene is known: M. Fuber and R. J. K. Taylor, J. Chem. Soc., Perkin Trans. 1, 1986, 1809.
6. An α-enynylation reaction of 2,6-dimethyl-2-cyclohexene-1-one enolate with hexachloro-1,3-butadiene was reported: A. S. Kende, P. Fludzinski, J. H. Hill, W. Swenson, and J. Clardy, J. Am. Chem. Soc., 106, 3551 (1984).
7. 4. The solution was passed through short silica gel column to remove traces of gallium salts, and was concentrated. The residue was purified by flash column chromatography (hexane) to give 12 (n = 1) (102 mg, 74%) and 13 (4 mg, 4%).