Reactivity Documentation
Acyl Halides, Sulfonyl Halides, and Chloroformates |
mixed with |
Organometallics |
Summary
- Flammable: Reaction products may be flammable
- Generates heat: Exothermic reaction at ambient temperatures (releases heat)
Details
Reactivity Predictions (for each pair of reactive groups)
Organometallics
Hazard Predictions
- Flammable: Reaction products may be flammable
- Generates heat: Exothermic reaction at ambient temperatures (releases heat)
The combination of acyl halides and organometallic compounds may result in an exothermic reaction. Caution should be used before proceeding. Further research of comparable examples in the literature or very small scale, carefully controlled experiments may be needed to fully assess compatibility.
Vinyl tributyltin reacts with arylsulfonyl halides in a palladium-catalyzed reaction to form vinyl sulfones (Roy, K.-M. 2000. Sulfones and Sulfoxides. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).
Carboxylic acid halides can be reduced to aldehydes using Na2[Fe(CO)4] (Collman's Reagent). Sodium halide salts are also produced (C. Elschenbroich, A. Salzer; Organometallchemie, Teubner Studienbucher, Stuttgart 1988, p. 285).
Organocopper, organolithium, and lithium dialkylcuprates react with sulfonylfluorides to form alkylsulfones (L. L. Frye, E. L. Sullivan, K. P. Cusack, J. M. Funaro, J. Org. Chem. 57 (1992) 697).