We show that if a locally compact group $G$ is non-discrete or has an infinite amenable subgroup, then the second dual algebra $L^1(G)^{**}$ does not admit an involution extending the natural involution of $L^1(G)$. Thus, for the above classes of groups we answer in the negative a question raised by Duncan and Hosseiniun in 1979. We also find necessary and sufficient conditions for the dual of certain left-introverted subspaces of the space $C_b(G)$ (of bounded continuous functions on $G$) to admit involutions. We show that the involution problem is related to a multiplier problem. Finally, we show that certain non-trivial quotients of $L^1(G)^{**}$ admit involutions.