THF is used as a solvent for Grignard reagents, but epoxides react with Grignard reagents. There is only a small difference between epoxides and THF, what causes the difference in reactivity towards Grignard reagents?
Answer
The difference between THF and epoxides is perhapse bigger than you might think. Due to the three-membered-ring of an epoxide, a lot of energy is 'stored' in ring strain. This destabilizes the stucture and is a driving force for a Grignard reaction (or any substitution on an epoxide).
The THF is a five-membered-ring, which is far more stable. This bond is simply an ether, that happens to be in a cyclic structure. Therefore it also reacts like an ether: not easily attacked by nucleophiles.
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