Baird first theorized the concept of anti-aromaticity in the context of the benzene triplet state, which is highly reactive. Wan and Krogh presented the concept of excited-state-antiaromaticity (ESAA) in 1985 in the context of a photosolvolysis reaction. Recently, ESAA has been observed experimentally by Kim and Hada and has been shown to lead to structural changes in the excited-states of benzenes and cyclooctatetraenes. Ottosson has argued that the alleviation of ESAA for benzene leads to the high reactivity of the excited state. A recent review by Karas and Wu states that systems with n → 𝜋 * character do not exhibit ESAA but rather preserve their aromatic character in the excited state. In this work, we theorize that the alleviation of pseudo-ESAA ultimately leads to an ultrafast geometric rearrangement of cyclopropenone rings and subsequent decarbonylation reaction on a <100 fs timescale.