Seeman, Jeffrey I.; Secor, Henry V.; Chavdarian, Charles G.; Sanders, Edward B.; Bassfield, Ronald L.; Whidby, Jerry F. published the artcile< Steric and conformational effects in nicotine chemistry>, Computed Properties of 33402-75-4, the main research area is alkylation kinetics nicotine; nicotine indomethylation stereochem; conformation indomethylation nicotine; NMR carbon 13 iodomethylated nicotine.
The stereoselectivity of iodomethylation of nicotine and 7 nicotine analogs having pyridine alkyl groups was determined by using 13C NMR. Alkylation at the pyridine (N) and at the pyrrolidine (N’) nitrogens was observed Two modes of N’-iodomethylation occur, cis and trans to the pyridine ring. N’-Iodomethylation occurs regioselectivity cis to the pyridine ring for all compounds examined The N/N’ and N’cis/N’trans ratios for the nicotine analogs were evaluated with regard to the orientation of the N’-Me group in the free base, conformational properties of the pyridine ring with respect to the pyrrolidine ring, and steric hindrance and buttressing effects on the pyridine nitrogen. The Curtin-Hammett principle and the Winstein-Holness equation are used to analyze these reactions.
Journal of Organic Chemistry published new progress about Alkaloids Role: RCT (Reactant), RACT (Reactant or Reagent). 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Computed Properties of 33402-75-4.
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