Can be used in place of Diiodomethane, in the Simmons-Smith cyclopropanation reaction: Bull. Chem. Soc. Jpn., 46, 892, 1895 (1973); Synthesis, 700 (1977); J. Org. Chem., 56, 6974 (1991); J. Am. Chem. Soc., 114, 2592 (1992); Tetrahedron Lett.. 34, 7157 (1993). Preferred to CH2I2 in the methylenation of allylic alcohols, resulting in a more complete reaction: J. Org. Chem., 54, 3525 (1989). The highly unstable ClCH2Li, generated and trapped in situ: Tetrahedron Lett., 835 (1984); 795 (1986), converts esters to chloromethyl ketones: J. Chem. Soc., Chem. Commun., 969 (1994). Adducts with ketones can be further lithiated, enabling reaction with electrophiles on carbon: J. Chem. Soc., Perkin 1, 3339 (1988).In the absence of added electrophile, the dilithio-derivatives undergo elimination to give alkenes in good yield: J. Chem. Soc., Chem. Commun., 1665 (1986).
