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Please login to access the full content or check if you have access via8.4.4.1.1 Variation 1: Removal of Hydrogen by Rubidium or Cesium Metal
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Streitwieser, A.; Xie, L., Science of Synthesis, (2006) 8, 1517.
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]
Meeeee 8 Meeeeeeeee ee Meeeeeeeeeee ee Meeeeeee ee Meeeee Meeee[8–88]
Meeeeeeeeeee Meeeeeeee
Meeeee Meeeeeeeeeeeeeeee (8, M8 = M; M = Me):[88]
Meeeeeeeeeeeeee (8.88 e, 88.8 eeee) eee eeeee ee Me eeeee (8.88 e, 8.8 eeee) ee MMM (88 eM) ee −88°M. Mee eeeeeee eee eeeeeee ee eeee ee ee, eee eee eeee eeeeee eee 8 e ee 88°M. Mee eeeeee eeeee eeee eee eeeeeeee eeeee eeeee eeee, e eeee ee eee MMM (88%) eee eeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeeeeeee (88 eM) eee eeeee. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeeee, eeeeee eeee eeeeeeeeeeee (8 ×), eee eeeee ee 88−8 Meee. M eeeee, eeee eee-eeeeeeeee eeeeee eee eeeeeeee. Mee eeeeeeee ee eee eeeeeee ee eeeeeeeeeeee ee Me8M, eee ee eeeeeee ee eee MMM; eeeee: 8.88 e (88%); ee >888°M (eee); MM (Meeee) ν̃: 8888 (e), 8888 (e), 8888 (e), 8888 (e), 888 (e), 888 (ee) ee−8.
References
[7] | Meee, M. M.; Meeee, M. M.; Meeeeeeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[8] | Meeeee, M. M.; Meeeee, M. M., M. Meee. Mee., Meeee., (8888), 888. |
[9] | Meeeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., M. Meee. Mee., Meeee., (8888), 888. |
[10] | Meee, M. M.; Meeeeeeeeee, M., Me., Meeeeeeeeeeeeee, (8888) 88, 888. |
[11] | Meeeeee, M.; Meeeeee, M.; Meeeeee, M., M. Meeeeeeee. Meee., (8888) 888, 88. |