Simmons smith reaction

Simmons Smith Reaction
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1. Simmons-Smith Reaction Olefin Cyclopropane CH 2 I 2 + Zn/Cu

2. Mechanism 2CH 2 I 2 + 2 Zn 2ICH 2 Zn I ( ICH 2 ) 2 Zn + ZnI 2 2ICH 2 ZnI C Zn I Zn I I [ ] I H H

3. Stereospecific Reaction Trans-Alkene Cis-cyclopropane Cis -Alkene Trans- cyclopropane

4. Examples

5. EtOOC-CH=N=N + - EtOOC-CH + N 2 .. CH- COOEt .. - COOEt Unstable - COOEt

6. R OEt R O O Β - Ketoester Cyclic Intermediate Et 2 Zn 2Eq. O-ZnEt 2 OEt O γ - Ketoester Cyclic Intermediate O O OEt OEt O R O-ZnEt 2 R

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