Hindered Rotation in N,N,N'-Trisubstituted Amidines

Article abstract of DOI:10.1002/ardp.19803130305

Alkylation of N,N'-dimethylbenzamidine (4) with chloromethyl methyl ether and allyl iodide leads to the formation of the N-trisubstituted amidines 5a and 5d; the lithium salt of 4 yields 5b and 5c with chloromethyl methyl sulfide and (chloromethyl)diethylamin, respectively.At temperatures up to 175 deg C no <1,3>sigmatropic rearrangement can be detected by (1)H-NMR spectroscopy; below room temperature a hindered rotation around the C-N single bond is observed.