Negative Enterprise Value Interpretations

I know there are other topics on this but am still a little confused. I also understand the formulas for enterprise value and how Cash > Net Debt + Equity Value could make an enterprise value negative.

Can someone please explain basic examples for why enterprise value might be negative for a company? Also if a company has an enterprise value of -$100 and you buy that company for a $100, are you technically paying $0 for it?

Thank you for your help.

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