Simmons – Smith Reaction

Bhingardive Pratiksha Shantaram

MES’s Abasaheb Garware College, Karve Road, Pune.
Introduction Regioselectivity Modification
The Simmons-Smith Reaction is an organic cheletropic Regioselectivity Simmons-Smith-type cyclopropanations
reaction involving an organozinc carbenoid that reacts of polyalkenes enabled by transition metal catalysis.
with an alkene (or alkyne) to form cyclopropane.
Simmons-Smith Reaction

Named After Howard Ensign Simmons & Jr.

Ronald D. Smith
Reaction Type Ring forming reaction
Substrate Olefines (Alkene)
Attacking Reagent ZnCu
Product Cylcopropane Reagent  Application
1. Iodomethylzinc Iodide. The Simmons-Smith Reaction can be used to
2. Et2Zn, CH2I2. cyclopropanate simple alkenes without complications.
Reaction
Stereo-Chemistry
Acknowledgement
CH2I2 + ZnCu Simmons and Smith found that (IZnCH2I) could be used
I would like thank Principal of Abasaheb Garware
Olefins Cyclopropane for the stereospecific conversion of alkenes to
College Mr. Buchade Sir for giving me this opportunity
cyclopropanes in 1958.
and also thanks to Chemistry Department and my
mentor Mrs. Gauri A. Khopate Madam.
Mechanism Pathway

References
1. Simmons, H.E. ; Smith R. D. J. Am. Chem. Soc.
1958, 80, 5323-5324.
2. Simmons, H.E. ; Org. React. 1973, 20, 1-133.
3. J. Worth, C. Uyeda, Chem. Sci., 2018, 9, 1604.