By Heinrich Zollinger
A serious, well-referenced and eminently readable creation to the chemistry of fragrant and heteroaromatic diazo compounds. hugely priceless reference for artificial natural chemists, business chemists and colour chemists. DLC: fragrant and heteroaromatic compounds.
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Additional info for Diazo Chemistry, Vol. 1, Aromatic and Heteroaromatic
28 Mikhail G. Voronkov and Klavdiya A. Abzaeva In 1964–1966, Satge and coworkers36,37 used reactions of alkylhalogermanes with amino lithium and organomagnesium derivatives to generate Ge N bonds. Satge and Baudet462 synthesized in 1966 hexaethyldigermazane by the reaction of Et3 GeCl and LiNH2 in THF. The extremely unstable Et3 GeNH2 was a probable intermediate in the reaction. At the same year Massol and Satge356 discovered that the ammonolysis of Et3 n GeHn Cl (n D 1, 2) led to the corresponding trigermylamines (Et3 n GeHn )3 N (when n D 1, Et2 GeHNHGeHEt2 was also formed).
In 1950, Johnson and Harris173 found that thermal decomposition of Ph3 GeH gave Ph2 GeH2 and Ph4 Ge. The diphenyldigermane product was also unstable and decomposed slowly even at room temperature, forming tetraphenylgermane as one of the products. Phenylgermane decomposed to Ph2 GeH2 and GeH4 354 at 200 ° C. The reaction proceeded instantly in the presence of AlCl3 even at room temperature. In contrast, the alkylgermanes R4 n GeHn were more stable and their stability toward thermolysis increased on decreasing the value of n276 .
R2 NC6 H5 C GeCl4 ! Cl3 GeC6 H4 NR2 Ð HCl H2 O ! 5 )n (3) In 1955, Seyferth and Rochow283 developed a nontrivial method of Ge Ge bond formation based on the insertion of a carbene (H2 C: formed from diazomethane) into a Ge Cl bond of GeCl4 to form ClCH2 GeCl3 . Later, Seyferth and coworkers284,285 extended this approach to the formation of the GeCH2 X (X D Cl, Br) group by the reaction of dihalocarbenes (generated from PhHgCX2 Br) with Ge H bonds. Kramer and Wright286,287 and Satge and Rivi´ere288 demonstrated the possibility of carbene (formed from diazomethane) insertion into the Ge H bond to give a Ge CH3 moiety.
Diazo Chemistry, Vol. 1, Aromatic and Heteroaromatic by Heinrich Zollinger