Their instability in the condensed phase is due to their ready disproportionation to aluminium and the respective trihalide: the reverse reaction is favored at high temperature (although even then they are still short-lived), explaining why AlF3 is more volatile when heated in the presence of aluminium metal, as is aluminium metal when heated in the presence of AlCl3. A stable derivative of aluminium monoiodide is the cyclic adduct formed with triethylamine, . Also of theoretical interest but only of fleeting existence are Al2O and Al2S. Al2O is made by heating the normal oxide, Al2O3, with silicon at in a vacuum. Such materials quickly disproportionate to the starting materials. Very simple Al(II) compounds are invoked or observed in the reactions of Al metal with oxidants. For example, aluminium monoxide, AlO, has been detected in the gas phase after explosion and in stellar absorption spectra. More thoroughly investigated are compounds of the formula R4Al2 which contain an Al–Al bond and where R is a large organic ligand. A variety of compounds of empirical formula AlR3 and AlR1.5Cl1.5 exist. The aluminium trialkyls and triaryls are reactive, volatile, and colorless liquids or low-melting solids. They catch fire spontaneously in air and react with water, thus necessitating precautions when handling them. They often form dimers, unlike their boron analogues, but this tendency diminishes for branched-chain alkyls (e.g. Pr"i", Bu"i", Me3CCH2); for example, triisobutylaluminium exists as an equilibrium mixture of the monomer and dimer. These dimers, such as trimethylaluminium (Al2Me6), usually feature tetrahedral Al centers formed by dimerization with some alkyl group bridging between both aluminium atoms. They are hard acids and react readily with ligands, forming adducts. In industry, they are mostly used in alkene insertion reactions, as discovered by Karl Ziegler, most importantly in "growth reactions" that form long-chain unbranched primary alkenes and alcohols, and in the low-pressure polymerization of ethene and propene. There are also some heterocyclic and cluster organoaluminium compounds involving Al–N bonds. The industrially most important aluminium hydride is lithium aluminium hydride (LiAlH4), which is used in as a reducing agent in organic chemistry.