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8.4.4.1.1 Variation 1: Removal of Hydrogen by Rubidium or Cesium Metal

DOI: 10.1055/sos-SD-008-01322

Streitwieser, A.; Xie, L.Science of Synthesis, (200681517.

Removal of hydrogen by rubidium or cesium metal provides direct access to many useful organocesium and -rubidium reagents which can be subsequently used in situ. (Diphenylmethyl)cesium has been prepared in tetrahydrofuran by reaction of diphenylmethane with cesium metal in a glovebox under an argon atmosphere.[‌7‌] The resulting (diphenylmethyl)cesium has been used to deprotonate other carbon acids in equilibrium acidity measurements. Other examples of hydrocarbon metalation by rubidium or cesium metal include the synthesis of prop-1-ynylrubidium and -cesium (1, M=Rb, Cs) in liquid ammonia,[‌8‌,‌9‌] metalation of (E)-hexa-1,4-diene to give hexadienylcesium (2) (not isolated, yield based on trimethylsilyl derivatization),[‌10‌] and the preparation of base-free rubidium and cesium cyclopentadienide and pentamethylcyclopentadienide (3, M=Rb, Cs; R1=H, Me) (Scheme 1).[‌11‌]

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