Titanium(IV) Chloride–Diazabicyclo5.4.0undec‐7‐ene

(TiCl4) [7550-45-0] Cl4Ti (MW 189.68) InChI = 1S/4ClH.Ti/h4*1H;/q;;;;+4/p-4 InChIKey = XJDNKRIXUMDJCW-UHFFFAOYSA-J (DBU) [6674-22-2] C9H16N2 (MW 152.27) InChI = 1S/C8H14N2/c1-2-6-10-7-3-5-9-8(10)4-1/h1-7H2 InChIKey = NPFWMKHDSNBLHS-UHFFFAOYSA-N (combination of reagents which allows the opening of epoxides to give chlorohydrins in the presence of acid labile groups1) Physical Data: see Titanium(IV) Chloride and 1,8-Diazabicyclo[5.4.0]undec-7-ene. Solubility: TiCl4: sol aromatic hydrocarbons, ether, THF, dioxane, chlorohydrocarbons. DBU: sol ethers, chlorohydrocarbons, aromatic solvents. Form Supplied in: TiCl4: colorless liquid, or as a crystalline complex with THF. DBU: colorless liquid. Preparative Methods: DBU (2 equiv) is added to a solution of the epoxide in dichloromethane. The mixture is cooled to −78 °C. TiCl4 (1 equiv) is then added and the mixture allowed to warm to rt. Handling, Storage, and Precautions: TiCl4 is corrosive and moisture sensitive. DBU is a flammable liquid. The combination reagent is moisture sensitive and reactions are best performed under a dry inert atmosphere. Solvents should be dried before use.