Diphenylmethoxy indole

A number of reactions of organomagnesium compounds with compounds containing nitrogen-nitrogen multiple bonds give products containing new carbon-nitrogen bonds [A, E], but few of them are useful in synthesis. The main exceptions are reactions with azides, and some reactions of diazonium salts. 

Reactions of Grignard reagents with azides, giving triazenes. have been known for many years [A]  

Yields are variable [A], but generally good yields were reported for a more recent study using azidomethyl phenyl sulfide, PhSCH,N, [18], In the examples where R = aryl, the triazenes were easily hydrolysed to the corresponding amines, R NH2. 

Variable yields of azo compounds were also obtained from reactions of Grignard reagents with diazonium salts, but benzenediazonium tetrafluoroborate gave acceptable yields from arylmagnesium bromides or t-butylmagnesium chloride in THF [19]  

Theilacke and W. Wegner, Newer Methods of Preparative Organic Chemistry (ed. W. Foerst) Vol. Ill, p. 303, Academic Press, New York, 1963. 

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