The response here can be regarded as a follow-up to ekkilop’s fine answer. It can be viewed as a generalization of that answer, and remains pertinent to the question being asked.
Let the term $m$-involution mean any complex square matrix $K$ for which $K^m=I$, where $m$ is an integer greater than $1.$ The usual involutory matrix case corresponds to the situation where $m=2.$ One question we may ask is, for a given square matrix $A$, what can we say about the set of $m$-involutory matrices that anti-commute with it? Let’s denote this set as $\tilde S_m\left( A \right)$.
Given $A \in \mathbb{C}^{n \times n},$ it is possible to establish the following result:
- Let $n=1$. If $A$ is the number zero, then $\tilde S_m\left( A \right)$ contains the $m$-th roots of unity. Otherwise, $\tilde S_m\left( A \right)$ is empty.
- Suppose $n>1$ and let $m>1$ be an odd integer. If $A$ is the zero matrix, then $\tilde S_m\left( A \right)$ is non-denumerable. Otherwise, $\tilde S_m\left( A \right)$ is empty.
- Suppose $n>1$ and let $m>1$ be an even integer. If the non-zero eigenvalues of $A$ come in pairs of opposite sign where the corresponding pairs have Jordan blocks of equal size, then the cardinality of the set $\tilde S_m\left( A \right)$ is non-denumerable. Otherwise $\tilde S_m\left( A \right)$ is empty.
Characterizing the sets to be empty or non-denumerable for $n>1$ may seem to be a rather weak statement, but note that this result contrasts, for example, with the set of $m$-involutions that commute with a fixed diagonalizable matrix $A\in \mathbb{C}^{n \times n}$ with distinct eigenvalues in which the case the cardinality of the set is $m^n.$
Note that the first and third cases together imply ekkilop’s observation. For the third case with $m=2$, if $n$ is odd then if $A$ is non-singular the Jordan blocks corresponding to nonzero eigenvalues of $A$ cannot all be paired up as positive - negative pairs of equal size. In other words, if $n$ is odd and $A$ is non-singular, then $\tilde S_2\left( A \right)$ must be empty: i.e., there are no involutory matrices $K$ that can anti-commute with $A$. Therefore, if $n$ is odd and $A$ anti-commutes with some involutory matrix $K$, then $A$ must be singular.
The theorem quoted above is trivial to prove for the first two cases. For the second case, we can simply observe that for an $m$-involutory matrix $K$ that anti-commutes with $A,$ we have that $A = K^mA = (-1)^mAK^m = (-1)^mA$, so if $m$ is odd it then follows that $\tilde S_m\left( A \right)$ is empty except when $A$ is the zero matrix.
For the third case, the argument is somewhat more involved. For that demonstration, the interested reader can find a proof in the paper "Some properties of commuting and anti-commuting m-involutions”. Perhaps more interesting is that this paper's Lemma 5.1, which is the main observation used in the proof, can be used to construct $m$-involutory matrices $K$ that anti-commute with a given matrix $A$, provided such $K$ exist.