We describe an effort to understand how singlet oxygen dissociates from several 1,4-polymethylene-naphthalene endoperoxides from a computational study. The number of methylene groups was varied from 20-30. An obvious problem is size, since large compounds cannot be computed at CCSD or QCISD levels. However, B3LYP/6-31+G(d)//AM1 and ONIOM(B3LYP/6-31+G(d):AM1) calculations seem to permit us to disentangle the energetics of ¹O₂ release from the rope skipping action of the polymethylene group. The challenges of computing and understanding ¹O₂ movement across an environment bearing a rotating chain will be discussed.