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Spivey, A. C.; Diaper, C. M., Science of Synthesis, (2003) 5, 129.
Deprotonation of acidic protons using lithium bases is a convenient method for the formation of organolithium reagents, which can subsequently be quenched with halogermanes to give α-amino-, e. g. 13, Scheme 4 [5] α-isocyano-,[34] α-imino-,[35] and α,α-diheteroalkylgermanes,[36,37] (the latter functioning as a masked acylgermane Section 5.1.16.4).[38] α-Alkoxyalkylgermanes 14 have been prepared from the corresponding α-alkoxyalkylstannanes via transmetalation using butyllithium,[39] whereas monolithium–halogen exchange or deprotonation has also been carried out using gem-dihalo and trihalo derivatives to give monohaloalkylgermanes and α,α-dihaloalkylgermanes respectively (such as 15 and 16 in Scheme 4). α-Halogermanes can be subsequently converted into the corresponding iodozincs,[40] which are known to be useful intermediates in organic synthesis.[41] Attempts to synthesize 1,1-dihaloallylgermanes using this methodology, however, are unsuccessful.[42]
Meeeee 8 α-Meeeeeeeeeeeeeeeeee Meeee Meeeeeeeeeeee Meeeeeee[88,88,88]
Meeeeeeeeeee Meeeeeeee
(Meeeeeeeeeee)(eeeeeeeeeeeeeee)eeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[88]
M 8.8 M eeee ee MeMe ee eeeeee (88 eM, 88 eeee) eee eeeee ee e eeeeeee eeee ee eMe8MM (8.88 e, 88 eeee) ee MMM (88 eM) ee −88°M eee eee eeeeeeee eee eeeeeeeee eee 88 eee. Mee eeeeeeeee MMM eeee eee eeeee ee e eeeeeee ee Me8MeMe (8.88 e, 88 eeee) eee (eeeeeeeeeeee)eeeeeeeeeeee (88 eeee) ee MMM (88 eM) ee −88°M. Mee eeeeeee eee eeeeeee ee eeee eeeeeeeeeee eee 8 e eee eeee eeeeee ee ee. Mee eeeeeeee eee eeeeeeee eeee eee. MM8Me (88 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM), eeeee (MeMM8), eee eeeeeeeeeeee ee eeeee. Mee eeeeeeeee eee eee eeeeeeeee ee eeee eee eeeeeee ee ee eee; eeeee: 8.8 e (88%); ee 88–88°M/8 Meee; MM νeee: 8888 ee−8 (M≡M); 8M MMM (MMMe8, δ): 8.88 (e, 8M), 8.88 (e, M = 8 Me, 8M), 8.88–8.88 (e, 8M), 8.88 (e, 8M).
References
[5] | Meeeee, M. M.; Meeeee, M.; Meeeee, M. M. M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[34] | Meeeeeee, M. M.; Meee, M. M., Meeee. Meee. Meee, (8888) 88, 888. |
[35] | Meeeeeee, M.; Meee, M.; Meeeeee, M., M. Meeeeeeee. Meee., (8888) 888, 888. |
[36] | Meeeeeee, M. M. M.; Meeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[37] | Meee, M.; Meee, M.; Meee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 888. |
[38] | Meeeeeeeee, M.; Meeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[39] | Meeeeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[40] | Meeeeeee, M.; Meeeeee, M. M., M. Meeeeeeee. Meee., (8888) 88, 888. |
[41] | Meeeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M., Meeeeee, (8888), 888. |
[42] | Meeeeeee, M.; Meeeee, M. M.; Meeeeeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 88. |
[43] | Meeeee, M.; Meeee, M.; Meee, M., Meeeeeeee, (8888), 888. |
[44] | Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeee, M., Meee. Mee., (8888) 888, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 88.