Every $A \in \text{GL}_n^+(\mathbb{R})$ (an invertible matrix with positive determinant) has a unique Polar decomposition: $A=OP$ where $O \in \text{SO}_n$, $P$ symmetric positive definite. The orthogonal polar factor is $O(A)=A(\sqrt{A^TA})^{-1}$ and the positive factor is $P(A)=\sqrt{A^TA}$.
Question:
Assume $O(A)O(B)=O(AB)$. Does it imply the $P(A),P(B)$ commute?
What about the converse? Does $[P(A),P(B)]=0 \Rightarrow O(A)O(B)=O(AB)$?
(It is easy to see a sufficient condition for $O(A)O(B)=O(AB)$ is that $P(A)$ commutes with $O(B),P(B)$. This question is a step towards seeing whether this condition is necessary) .
Motivation:
This question has a geometric nature, since $O(A)$ is the closest matrix in $\text{SO}_n$ to $A$ (w.r.t to the Frobenius norm). Thus, it reflects the "rotational part" of $A$; We can think of it as the best "isometric approximation" of $A$. If we know these two approximations for $A,B$ it is natural to compose them and to ask if we obtained in this way the best approximation to $AB$.
Partial result:
If $B > 0$ is symmetric positive definite, then $O(A)O(B)=O(AB) \iff [P(A),B]=[P(A),P(B)] =0$
Proof:
Let $A=O_AP_A$ be the polar decomposition of $A$. Then:
$$ O_AO_B=O_{AB} \iff O_A=O_{AB}=O_{O_AP_AB} \iff O_AP_AB= O_A\hat P$$ for some $\hat P >0$.
Thus, $ O_AO_B=O_{AB} \iff $ $P_AB > 0 \iff [P_A,B]=0$.
A fairly random computation with Mathematica suggests that the answer is no. A numerical counterexample is $$A=\begin{pmatrix}1&0.7\\0.2&4.9296967794602\end{pmatrix},\,\,\,\,B=\begin{pmatrix}1&0.3\\0.2&5\end{pmatrix},$$ which you can check with the commands
(Here, m1 is A, m2 is B, m3 is AB. The polar decompositions are m1=a1.p1, m2=a2.p2, m3=a3.p3, and we check that a1.a2-a3 is zero up to precision while p1.p2-p2.p1 is non-zero.)