Simmons-Smith Reaction

H. E. Simmons, R. D. Smith, J. Am. Chem. Soc. 80, 5323 (1958).

Stereospecific synthesis of cyclopropanes by treatment of olefins with methylene iodide and zinc-copper couple:

Synthetic applications: J. Long et al., Tetrahedron Lett. 46, 2737 (2005). Mechanistic studies: M. Nakamura et al., J. Am. Chem. Soc. 125, 2341 (2003). Reviews: H. E. Simmons et al., Org. React. 20, 1 (1973); C. Girard, J. M. Conia, J. Chem. Res. Synop. 1978, 182; W. Ratier et al., ibid. 179; A. Sele et al., Helv. Chim. Acta 62, 866 (1979); J. Joska, J. Fajkos, Collect. Czech. Chem. Commun. 46, 2751 (1981); V. K. Aggarwal et al., Eur. J. Org. Chem. 2002, 319-326.