Conversion of acid chlorides to substituted acetylenes with tungsten alkylidynes

Organometallics

Volumn 24, Issue 19, 2005, Pages 4684-4686

  Connell, Brian T ^a   Kirkland, Thomas A ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ALKYLIDYNES;

ACETYLENE; SYNTHESIS (CHEMICAL); TUNGSTEN;

CHLORINE COMPOUNDS;

EID: 25444507715     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050352k     Document Type: Article

References (22)

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9. Unsubstituted acetylenes can be synthesized from aldehydes, but multiple steps are required to obtain substituted acetylenes. For examples, see: (a) Matsumoto, M.; Kuroda, K. Tetrahedron Lett. 1980, 21, 4021-4024.
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15. Standard reaction conditions for all acetylene syntheses: Under an atmosphere of argon, 1.1 equiv of tungsten alkylidyne (0.1 M in benzene) was treated with 1.0 equiv of the indicated acid chloride. After stirring at rt for 2 h, the cloudy reaction mixture was directly filtered through a plug of silica to remove the metal salts and provide the pure acetylene product.
16. For some reviews of this process, see: (a) Schrock, R. R. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 1, pp 173-189.
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