In investigating and seeking to mimic the reactivity of trimethylaluminium (TMA) with synthetic, ester-based lubricating oils, the reaction of methyl propionate $1$ was explored with 1, 2 and 3 equivalents of the organoaluminium reagent. Spectroscopic analysis points to the formation of the adduct $1$ (TMA) accompanied only by the low level 1:1 production of Me$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$AlOCEtMe$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$ $2$ and Me$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$AlOMe $3$ when an equimolar amount of TMA is applied. The deployment of excess TMA favours reaction to give $2$ and $3$ over $1$(TMA) adduct formation and spectroscopy reveals that in hydrocarbon solution substitution product $2$ traps unreacted TMA to yield $2$(TMA). The $\mathrm{<mrow\; data-mjx-texclass="ORD">1</mrow>}$H NMR spectroscopic observation of two Al-Me signals not attributable to free TMA and in the ratio 1:4 suggests the formation of a previously only postulated, symmetrical metallacycle in Me$\mathrm{<mrow\; data-mjx-texclass="ORD">4</mrow>}$Al$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$ (μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-Me)(μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-OCEtMe$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$ ). In the presence of $3$, $2$(TMA) undergoes thermally induced exchange to yield Me$\mathrm{<mrow\; data-mjx-texclass="ORD">4</mrow>}$Al$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$(μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-OMe)(μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-OCEtMe$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$) $4$ and TMA. The reaction of methyl phenylacetate $5$ with TMA allows isolation of the crystalline product Me$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$AlOCBnMe$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$ (TMA) $6$(TMA), which allows the first observation of the Me$\mathrm{<mrow\; data-mjx-texclass="ORD"></mrow>}$ Al$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$(μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-Me)(μ$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$-OR) motif in the solid state. Distances of 2.133(3) Å (Al-Me) and 1.951 Å (mean Al-Me) are recorded. The abstraction of TMA from $6$(TMA) by the introduction of Et$\mathrm{<mrow\; data-mjx-texclass="ORD">2</mrow>}$O has yielded $6$, which exists as a dimer.