Illustrated Glossary of Organic Chemistry

Simmons-Smith reaction: A name reaction in which a carbenoid adds to an alkene or alkyne to form a cyclopropane.




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Diiodomethane

Organozinc carbenoid

Cyclohexene

Bicyclo[4.1.0]heptane
This Simmons-Smith reaction begins with the halogen-metal exchange between diiodomethane (methylene iodide) and zinc (in a zinc/copper alloy) to produce a reactive intermediate organometallic carbenoid. This carbenoid then undergoes cycloaddition with the pi bond of cyclohexene (an alkene) to produce the cyclopropane ring of bicyclo[4.1.0]heptane.