Iodo-2-trimethylsilylmethyl- 1-propene

(a) Wichterle, O. Prochazka, J. Hofmann, J., Collect. Czech. Chem. Commun. 1948, 13, 300. (b) Review House, H. O. Modem Synthetic Reactions, 2nd ed Benjamin Menlo Park, CA, 1972 p 611. 

Preparative Method from the corresponding mesylate upon treatment with sodium iodide in acetone. The mesylate can be prepared from the commercially available alcohol. Purification distillation in the dark (25°C/0.5 mroHg, trap at -78 °C).2 

Handling, Storage, and Precautions can be stored in the dark at —20 °C for up to 3 months without significant deterioration.  

Dipolar Synthon for TVimethylenemethane. The most common use of this reagent is as a 1,3-dipolar synthon for trimethylenemethane (TMM) (eq 1).  

The dipolar character is unmasked in two separate synthetic steps. In the first, the synthon reacts at the positive end upon treatment with a nucleophile such as an enolate or metalloenamine.  

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Related Reagents. 3-Acetoxy-2-trimethylsilylmethyl-l-propene 1 3-Iodo-2-trimethylsilylmethyl-l-propene. 

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