Organometals butyllithium

Benzocyclobutene, Butyllithium, Potassium fert-butoxide Adcock, W. et al., J. Organomet. Chem., 1975, 91, C20... 

C. Elschenbroich, Metalation of Dibenzenechromium by V,V,V ,V -Tetramethy-lethylenediamine Complexes of n-Butyllithium and Phenyllithium, J. Organomet. Chem. 14, 157-163 (1968). 

In the polymerization of methacrylonitrile initiated by butyllithium, the organometal is bound to nitrile groups [137]... 

Methoxy-l-phenyl-l-propyne in anhydrous ether added at -75° under argon to 2 moles butyllithium in the same solvent, stirred 15 min., 1 mole ethyl bromide in ether added slowly, stirred 15 min., then trimethylsilyl chloride in ether added, allowed to warm to room temp, with stirring, the soln. of the intermediate allenyl ether (Y 82% if isolated) treated with 20%-HCl, and refluxed 5 hrs. product. Y 76%. F. e. s. Y. Leroux and R. Mantione, J. Organometal. Chem. 30, 295 (1971). 

A soln. of benzeneselenyl bromide in tetrahydrofuran added dropwise at room temp, under Ng to a stirred soln. of 2 equivalents methylenetriphenylphosporane prepared in tetrahydrofuran from methyltriphenylphosphonium bromide and a hexane soln. of n-butyllithium, after 0.5 hr. stirring benzaldehyde added, and refluxed 1 hr. product. Y 98%. F. e. and method s. N. Petragnani, R. Rodrigues, and J. V. Comasseto, J. Organometal. Chem. 114, 281 (1976). 

X10" M seo-butyllithium with 8.67 x 10 M styrene in cyclohexane solution at40°C. From Bywater, S. Worsfold, D. J.d Organometal. Chem. 1967, tO, 1 reprinted by permission of Elsevier Science Technology Journals. 

Organometals add onto strained triple bonds with particular ease. -Butyllithium reacts with cyclooctyne at -75 °C slowly and at 0 °C instantaneously. The important... 

Not only silcon, but also any other element of the second or a higher periodic row is able to stabilize electron excess and hence to facilitate organometal addition onto contiguous multiple bonds. For example, both dibutylvinylphosphine and diphenylvinylphosphine react with n-butyllithium or ter/-butyllithium to form the corresponding adducts. ... 

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