I have just read a topic on mathoverflow about man vs. machine in mathematics. The topic was inspired by the recent victory of Alpha Go over the World Go Champion, Lee Sedol. It reminded me of an article I read (possibly on American Mathematical Monthly) about translating Jordan Curve Theorem into machine-checkable form.
I would love to hear about why is it so hard, generally, to translate a proof of some theorem so that a machine can check it. What is fundamentally different between, says, the Four Color Theorem and Jordan Curve Theorem that makes it a lot harder for machine to deal with the later?
EDIT: I have found a wonderful related link Why is it hard to prove Jordan Curve Theorem in the case of Koch snowflake.
Another example is Gonthier's recent proof of Feit–Thompson theorem. It would be too long to answer your question in detail, but this link (in French) COQ ET CARACTÈRES, Preuve formelle du théorème de Feit et Thompson, contains several relevant references.
In particular, A Special Issue on Formal Proof of the Notices of the AMS gathers four articles:
Formal Proof by Thomas Hales
Formal Proof--The Four-Color Theorem by Georges Gonthier
Formal Proof--Theory and Practice by John Harrison
Formal Proof--Getting Started by Freek Wiedijk