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N,N′,N′′-peralkylated guanidinium chlorides and N,N′,N′′-peralkylated guanidines were prepared from N,N′-peralkylated chloroformamidinium chlorides. The alkylation of the guanidines affords N,N′,N′′-persubstituted guanidinium chlorides bromides, iodides, alkylsulfates, and tetrafluoroborates. Guanidinium tricyanomethanides and tetracyanopropenides were prepared from the chlorides and iodides by anion metathesis. The reaction of guanidinium halogenides with borontrifluoride etherate, triethyloxonium tetrafluoroborate or sodiumtetrafluoroborate delivers guanidinium tetrafluoroborates. Guanidinium saccharinides, cyanates, thiocyanates, trifluoromethansulfonates, bis(trifluormethansulfonyl)imides, hexacyanoferrates(II/III), tetracyanonickolates and tetrathiocyanatocobaltates were prepared from the corresponding guanidinium chlorides and tetrafluoroborates by anion exchange. [ABSTRACT FROM AUTHOR]

Bis[bis(dibutylamino)methylen]hydrazine 8 is prepared from N,N,N′,N′-tetrabutylchloroformamidinium chloride (4c) and hydrazine. Bromine transforms 8 to the heterocyclic guanidinium salt 15a which is isolated as tetraphenylborate. From N,N,N′,N′-tetraalkylchloroformamidiniumchlorides and ethylendiamine the diguanidines are prepared which are alkylated to give diguanidinium salts, From these salts guanidinium salts can be prepared by anion metathesis with tetraphenylborate-, iodide-, hexafluorphosphate-, trifluoromethansulfonat-, bis(trifluormethansulfonyl)imide and tricyanmethanide as counteranions. The structure of the compounds 15 and 17b is confirmed by crystal structure analyses. [ABSTRACT FROM AUTHOR]