Ring opening of epoxides

7 real reactions from the literature, on epoxides, Grignard reagents and secondary sulfonate esters. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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1. Epoxide opening: ethylene oxide (an epoxide) with 46% HBr gives 2-bromoethanol (the halohydrin).

   Epoxide openingOrg. Synth. Coll. Vol. 1, p. 117

2. Epoxide opening: a Grignard reagent with CH3CH2OCH2CH3 gives the ring-opened product.

   Epoxide openingOrg. Synth. Coll. Vol. 1, p. 306

3. Epoxide opening: an epoxide with Camphor Sulfonic Acid (CSA); pKa = 1.2; CH2Cl2 gives the ring-opened product.

   Epoxide openingJ. Am. Chem. Soc. 1989, 111, 5330

4. Epoxide opening: an epoxide with MeNH2; MeOH gives the tertiary alcohol.

   Epoxide openingJ. Med. Chem. 2000, 43, 4045

5. Epoxide opening: a secondary sulfonate ester with NH3 / NH4OH, iPrOH gives the secondary alcohol.

   Epoxide openingPCT Int. Appl. WO2008007109

6. Epoxide opening: 2,2-diphenyloxirane (an epoxide) with HClO4 gives 2,2-diphenyl-2-prop-2-enoxyethanol (the primary alcohol).

   Epoxide openingJ. Med. Chem. 2008, 51, 6359

7. Epoxide opening: an epoxide with J Med Chem 2000 43 4045 gives the tertiary alcohol and dinitrogen-N-sulfide (the ring-opened product).

   Epoxide openingRealOChem worksheet