1,1-Dichloroallyllithium

[51522-97-5] C3H3Cl2Li (MW 116.90) InChI = 1S/C3H3Cl2.Li/c1-2-3(4)5;/h2H,1H2;/q-1;+1 InChIKey = GRFACWRHHUXZSD-UHFFFAOYSA-N (ambient allyl anion; reacts with a variety of electrophiles to give α- and/or γ-substituted products;1-5 can serve as a ketone annulating agent to form cyclopentenones;5 an equivalent of chlorovinyl carbene6) Solubility: sol THF. Preparative Methods: 1,1-dichloroallyllithium 2 can be prepared1 by the lithium–halogen exchange reaction between n-butyllithium and 3,3,3-trichloropropene 1 at −105 °C (eq 1), but transmetalation of 3,3-dichloro-2-propenyltriphenyllead 3 with n-butyllithium in THF at −95 °C is cleaner (eq 2).1 (1) (2) Handling, Storage, and Precautions: highly unstable; generated only at −95 °C, in the presence of electrophiles in an inert atmosphere. Use in a fume hood.