I am wondering about this. A well-known class of functions are the "involutive functions" or "involutions", which have that $f(f(x)) = x$, or, equivalently, $f(x) = f^{-1}(x)$ (with $f$ bijective).
Now, consider the "anti-involution" equation $f(f(x)) = -x$. It is possible for a function $f: \mathbb{C} \rightarrow \mathbb{C}$ to have $f(f(z)) = -z$. Take $f(z) = iz$.
But what about this functional equation $f(f(x)) = -x$ for functions $f: \mathbb{R} \rightarrow \mathbb{R}$, instead of $f: \mathbb{C} \rightarrow \mathbb{C}$? Do such functions exist? If so, can any be described or constructed? What about in the more general case of functions on arbitrary groups $G$ where $f(f(x)) = x^{-1}$ (or $-x$ for abelian groups), $f: G \rightarrow G$? Can we always get such $f$? If not, what conditions must there be on the group $G$ for such $f$ to exist?