22751-75-3Relevant articles and documents
N-acyl- and N-sulfonylformamidines from cyanamides and carbodiimides by hydroalumination and subsequent treatment with electrophiles
Hellmann, Johannes,Rhotert, Ines,Westenberg, Hauke,Froehlich, Roland,Wibbeling, Birgit,Uhl, Werner,Wuerthwein, Ernst-Ulrich
, p. 3356 - 3368 (2013/07/05)
Hydroalumination of cyanamides 1 with di(isobutyl)aluminium hydride affords intermediate compounds 3, which have dimeric structures in the solid state with four-membered Al2N2 heterocycles and exocyclic N=C double bonds. The reactions of 3 with acyl chlorides yield N′,N′- disubstituted N-acylformamidines 5, whereas reaction with sulfonyl chlorides give the corresponding N-sulfonylformamidines 7. In contrast, carbodiimides 8 react with dialkylaluminium hydrides R2AlH (R = tBu, iBu) to give compounds 9 in which one C=N bond of the carbodiimide is reduced to form an amidinate ligand and a second molecule of the hydride is coordinated through an Al-N and an Al-H-Al bond. Treatment of 9 with acyl chlorides yields N,N′-disubstituted N-acylformamidines 10, whereas reaction with sulfonyl chlorides gives the corresponding N-sulfonylformamidines 11. In a simple one-pot procedure cyanamides are converted into N′,N′-disubstituted N-acyl- or N-sulfonylformamidines by hydroalumination and subsequent treatment with acyl- or sulfonyl chlorides. Carbodiimides react similarly, forming N,N′-disubstituted N-acyl- and N-sulfonylformamidines. The intermediate aluminium compounds and several products were characterised, including by X-ray crystallography. Copyright
