Unformatted text preview: gives trans-epoxide. • Formation of Epoxides-Internal SN2 via Halohydrin : An alternative method for epoxide formation involves intramolecular SN2 reaction of a halohydrin. Like any SN2 reaction, the intramolecular SN2 reaction of a halohydrins is stereospecific. • Reactions of Epoxides-Acidic Cleavage : Upon exposure to aqueous acid, epoxides undergo stereospecific ring cleavage to give anti-1,2-diols. Markovnikov regiochemistry is observed. • Reactions of Epoxides-Basic Cleavage : Upon exposure to nucleophiles under basic conditions, strain relief drives opening of the epoxide with attack at the less substituted terminus. This regio- and stereospecific transformation works for epoxides only, i.e. not normal ethers....
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- Fall '08
- Reaction, strain relief, normal ethers