Simmons–Smith reaction

The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith. It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific.

Simmons-Smith reaction
Named after Howard Ensign Simmons, Jr.
Ronald D. Smith
Reaction type Ring forming reaction
Reaction
Organozinc carbenoid
+
Alkene/Alkyne
Cyclopropane
Conditions
Identifiers
Organic Chemistry Portal simmons-smith-reaction
RSC ontology ID RXNO:0000258
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