Oxidation of the (3)-1, 7-dicarba-nidododecahydroundecaborate (1

New Palladium-Catalyzed Cross-Coupling Routes to Carbon Functionalized Metallatricarbadecaboranes. Ariane Perez-Gavilan , Patrick J. Carroll , and Lar...
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Inorganic Chemistry TABLE I REACTION OF AMMOSIA-FREE CHLORAMIXE WITH ~,~-DIMETHYLHUDRAZINE Products, mmol----.

7 -

---Reactantsa, 1,l-Dimethylhydrazine

mmol--. Chloramine

Ammonium chloride

Triazanium Tetramethylchloride 2-tetrazene

30.0 (12.3) 30.0 ( 0 . 9 ) 24.7 30.0 (0.4) 24.9 29.8 (15.2) 60.2 ( 4 4 . 0 ) 30.0 (0.0) 23.6 30.0 ( 0 . 0 ) 60.2 (12.5) 37.6 5 Figures shown in parentheses indicate unreacted.

4.9 11.2 5.3 8.4 7.4 8.4 11.0 18.8 mmoles recovered

+ NHzCl +I(CHa)2X(NH2)2]Cl (CHa)?NNH- + + C1(CH3)zNNHz + NHrCl--+ (CH3)nNX< + iVH4Cl (CHa)zNX"z

(CHa)ziVKH2

+ NHzC1+

"3'.

(1) (2)

(3)

The dimethylazamine fragments in eq 3 could then combine to give tetramethyl-2-tetrazene, or the free radicals formed in eq 2 might combine to yield 1,1,4,4-tetramethyltetrazane, which could be further dehydrogenated'O by chloramine to give tetramethyl-2-tetrazene. The NH3+ species shown in eq 2 may then either react with the radicals formed in (2) to yield the dimethylazamine radical, (CH&NN