SiMe,,14). Thus the reaction of Me,GeBr with Li(MeN,H,) and with LiN2H3 gave mixtures of disubstituted isomers, 5a and b, and 70 and b, respectively, rather than mono-substituted derivatives. Reactions of Me,GeCI, gave (i) an unresolvable, highly condensed product with LiN,H,; (ii) the high molecular weight compound 11, with Li(MeN2H2); and (iii) the cyclic trigermazane 12 with Me2NNHLi; the extent of selfcondensation is a function of the degree of substitution of the hydrazine moiety. Reactions with protic reagents (H20, MeOH, anhydrous HCI) effect cleavage of the Ge-N bond in germylhydrazines. New compounds were characterized on the basis of i.r., n.m.r., and mass spectral measurements.
Results and Discussionlithium amide (9, 10) or hydrazide (1 l), howAminogermanes (11, aminosilanes (21, and ever, is generally effective in the synthesis of silylhydrazines (2) may be prepared by the metalloid-nitrogen systems. In the synthesis of aminolysis and hydrazinolysis of the appro-a lithium hydrazide salt via the reaction of priate metalloid-halogen bond, the halogen butyllithium with an a p~r o~r i a t e h~d r a z i n e (1 1 1, displacement reaction being favored by the an excess of hydrazine must be used to preclude simultaneous formation of an ionic, poorly formation of di-lithio salt, and the excess must soluble hydrohalide salt; an added strong base be the product before adding may be used for the latter purpose (2, 3), in bromogermane and solvent (ether); without this cases where the amine or hydrazine is very latter precaution, much hexamethyldigermane weakly basic. The hydrazinolysis of the Ge-x is found. Using appropriate lithium hydrazide bond is difficult to effect, even in the presence and Or Me2GeC12, of the of strong base, in contrast to the facile reactions ) were exof the Si-X bond (2). Both halo-silanes (4) cept for (eqs. ' and 2). For personal use only.