Pk. Sarma et Pj. Das, SYNTHESIS AND REARRANGEMENT OF 3-(N-INDOLINO)-1-ARYLTRIAZENES TO 5-ARYLAZOINDOLES, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(12), 1995, pp. 1092-1094
Indoline couples with aryldiazonium chlorides at pH 5 to give 3-(N-ind
olino)-1-aryltriazenes which undergo rearrangement in the presence of
chloranil to give 5-arylazoindoles. Formation of the triazene is not o
nly dependent on the pH but also on the nature of the substituent on t
he phenyl ring of the aryldiazonium ion.