Simmons–Smith reaction
| Simmons-Smith reaction | |||||||||
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| Named after | Howard Ensign Simmons, Jr. Ronald D. Smith | ||||||||
| Reaction type | Ring forming reaction | ||||||||
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| Organic Chemistry Portal | simmons-smith-reaction | ||||||||
| RSC ontology ID | RXNO:0000258 | ||||||||
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.