50707-40-9Relevant academic research and scientific papers
Novel one-pot synthesis of thiophenols from related triazenes under mild conditions
Khazaei, Ardeshir,Kazem-Rostami, Masoud,Moosavi-Zare, Ahmadreza,Bayat, Mohammad,Saednia, Shahnaz
experimental part, p. 1893 - 1896 (2012/09/22)
In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines. Georg Thieme Verlag Stuttgart · New York.
STRUCTURAL EFFECT ON THE MECHANISTIC PATHWAY OF THE DECOMPOSITION OF 3-ALKYL-1-ARYLTRIAZENES: A KINETIC STUDY
Laila, Abdulhameed A. R.
, p. 453 - 456 (2007/10/02)
A kinetic study of the reaction between 3-alkyl-1-aryltriazenes and substituted acetic acids has been made in solvent acetone over the temperature range 21-37 deg C.Ea is 17.3 +/- 0.3 kcal mol-1 and log A is 10.3 +/- 0.1.Influence of the substituents on the reaction rate has been analyzed.The Hammett correlation with ? gave a ρ value of -0.96 for para-aryl substituted triazenes and +0.35 for meta- and para-substituted phenylacetic acid.The rate of decomposition of triazenes is also affected by changing the alkyl group.From these results a duality in mechanism is proposed; first, a simultaneous protonation and alkyl group expulsion to be the rate-determining step when R is tertiary, benzylic and possibly secondary.Secondly, a concerted mechanism for the protonation of nitrogen and cleavage of the N-R bond for primary alkyl groups.
