Kinetische Daten des thermischen Zerfalls von Diazoniumsalzen in sauren Lösungen

Stability of 1-naphthalenediazonium ion in solution. Complexation and decomposition of 1-naphthalene- diazonium tetrafluoroborate in the presence of crown ethers and acyclic polyethers in 1,2-dichloroethane and the gas phase under fast atom bombardment conditions

“…5 A great number of publications, many wide reviews and even several books concerned with arenediazonium compounds have been published. [2][3][4][5][6][7][8] The thermal dediazoniation of arenediazonium ions has versatile applications in synthetic chemistry in the preparation of many widely different compounds. 2,3,6 It has been shown that thermal dediazoniations of aromatic diazonium salts involve a variety of mechanisms, heterolytic and homolytic, and small modifications to the reaction conditions (solvent, substituent, pH, atmosphere, addition of other solvents or substrates) may change the mechanism and products drastically.…”

“…2,3,6 It has been shown that thermal dediazoniations of aromatic diazonium salts involve a variety of mechanisms, heterolytic and homolytic, and small modifications to the reaction conditions (solvent, substituent, pH, atmosphere, addition of other solvents or substrates) may change the mechanism and products drastically. 2,3,[5][6][7][8] Nevertheless, publications describing thermal dediazoniation of naphthalenediazonium salts are surprisingly very few. 6,9 Host-guest complexation has been studied with great interest in recent decades owing to its many possible applications, e.g.…”

The Structural Influence in the Stability of Polymer‐Bound Diazonium Salts

“…Chlorine in ortho position to the linkage on the resin stabilises the diazonium resin. The size of the counterion plays an important role in the stability; bigger ones give more stability than smaller ones (10,11,12).…”

“…By substituting Equation (2) into Equation (11) and dividing both sides with the maximum values in order to normalize them, one obtains, after simplifying the constants DSC Total and A i , Equation (12).…”

“…In 1952 Lewis [11] and Hinds found that the decomposition of 4-nitrobenzenediazonium ion in water is proportional to the concentration of the added nucleophile. Although various other examples favor an S N 2 mechanism, the effect of substitution as determined by Crossley and later reconfirmed by Schulte-Frohlinde and Blume [12] cannot explain this mechanism. Instead of an increase of decay caused by substituents (e.g., 4-NO 2 ), as required for such a mechanism, nearly all substituents in metaor para-position led to a higher stability.…”