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Intermediate between these are the derivatives of Li, Be, Mg and Al which are associated through alkyl or aryl bridges. In contrast to diborane, B2 H6 , trimethylborane is monomeric in the vapour and also in the condensed states. The methyl groups are arranged trigonally in a plane about the boron atom. The boron atom has an empty 2p orbita) and consequently acts as a Lewis acid, forming complexes with electron pair donors such as amines, phosphines or hydride ion. Hydrogen readily forms bridges between boron atoms, for instance in tetramethyldiborane or in diborane itself.

____ _ 1, 1 ' ' 1 1 1 1 1 1 1 '' 1 ' 1 ~::;; (b) (c l ( d) Fig. 4 (a) Unit cel! of methyllithium. The (CH,Li) 4 tetramer. (After E. C. Lucken. ]. Organometal. Chem. (1964) l, 197. (b) The Li 4 C4 skeleton of the tetramer viewed approximately along one of threefold axes. 2C 6 H6 • Cyclohexyl groups occupy six of the eight triangular faces of the octahedron- only two shown. 2. Aggregation of organolithiums, (RLi)n in solution RLi MeLi EtLi Bu"Li su•u Bu1Li PhLi Menthyl Li Solvent Paraffins or cyclohexane Benzene or toluene Diethyl ether Tetrahydrofuran Insol Insol 4 4 4 4 4 4 4 4 2 2 6 4-6 4 4 2 6 6 4 4 -Not known to author.

Aromatic hydrocarbons containing two or more benzene rings joined (biphenyl. terphenyls ). conjugated ( 1, 4-diphenylbutadiene) or fused (naphthalene, anthracene, phenanthrene) react with alkali metals without loss or transfer of hydrogen. The formation of these addition compounds is facilitated by donor solvents such as tetrahydrofuran or 1, 2-dimethoxyethene. The products are highly coloured; their formation is accompanied by the transfer of one or more electrons from the alkali metal to the lowest unoccupied molecular orbita!

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