Chemisch induzierte dynamische kernpolarisation im system phenyldiazoniumetrafluoroborat/NaBH4 nachweis des arylradikals bei reaktionen vom typ der gomberg-arylierung

Dediazoniations of Arenediazonium Ions in Homogeneous Solution. Part XIV. 15N‐CIDNP. Investigation of the reactions of diazonium ions in weakly alkaline aqueous solutions

“…P Ar-0-Nz-Ar P P = products (hydrogen abstraction) and azoarenes 9 (reaction with 1 or 4) are indeed found [7]. This has been already demonstrated in earlier work [3] [4] for organic solvents.…”

Phenyldiimine in the Reduction of Diazonium Salts by Sodium Tetrahydridoborate

“…Hofmann[81, and Heesing [9] have established the formation of phenyldiimine on decomposition of the salt (3), its esters, and other derivatives. Numerical data for the decomposition of (3) are in reasonable agreement with those for the reduction of (2) but differ widely from those obtained for reactions known to proceed by way of phenyl radicals. It is thus demonstrated that reduction of diazonium salts with NaBH, involves an intermediate that reacts with methanol in the same manner as phenyldiimine.…”

“…Reaction of phenyldiazonium tetrafluoroborate (2) in methanol with copper powder at 0°C affords benzene in 62% yield. In CH,OD the benzene contains 1.6% deuterium, in CD,OH 54%, and in CD,OD 81% (see Table).…”