The concept of spacing functional groups along the backbone of hydrocarbon segments to obtain PE-like materials traces back to 1940, when Carothers' reported that polyesters and polyamides containing long-chain aliphatic segments displayed higher degrees of crystallinity, higher melting temperatures, greater hydrophobicity, and increased stiffness as the length of the aliphatic segments increased; i.e., the materials became more PE-like. Based on this general principle, many PE mimics have since been synthesized, typically via step-growth polymerization reactions (e.g., polycondensation or acyclic diene metathesis polymerization). Much less attention has been paid to the synthesis of PE mimics using chain polymerizations, despite the fact that most HDPE is synthesized using such mechanisms. A few examples of PE mimics prepared via ring-opening metathesis polymerization (ROMP) have been reported; however, chemical recycling of such polymers has not, to our knowledge, been demonstrated. Furthermore, regardless of whether step-growth or chain-growth mechanisms are used, the cleavable bonds introduced into PE and PE-like materials have so far been based on C-O (e.g., esters, orthoesters, and carbonates) and C=C bonds, which offer a limited range of selective cleavage reactions and in some cases may introduce hydrolytic, photo, and/or thermal instability. To further build upon the diversity of deconstructable PE materials, it would be advantageous to explore alternative cleavable bonds to achieve orthogonal properties and potentially enable new pathways for chemical recycling.