109477-06-7Relevant academic research and scientific papers
Rigid core vinamidinium salts and their N,N′-rotamers
Ostercamp, Daryl L.,Dinh, Yen,Graff, David,Wiles, Sarah
, p. 3099 - 3105 (2007/10/03)
The power of proton magnetic resonance spectroscopy to unravel stereochemical details is amply demonstrated. O-Methylation of 3-methylamino-5,5-dimethyl-2-cylohexen-1-one (1a) produces stable diastereomers, (Z)- and (E)-N-(3-methoxy-5,5-dimethyl-2-cyclohexen-1-ylidine)-N-methylaminium iodide (2a). As predicted by computation and confirmed by spectroscopy, the (Z)-vinylogous imidate salt predominates. Reaction of 2a with primary and secondary amines furnished a number of vinamidinium salts, including N-(3-methylamino-5,5-dimethyl-2-cyclohexen-1-ylidene)-N-methylaminium iodide (3a). Two rotamers of 3a were identified and characterized. A substantial number of additional compounds 2 and 3 are included in the study.
