21446-45-7Relevant academic research and scientific papers
Steric and Conformational Effects in Nicotine Chemistry
Seeman, Jeffrey I.,Secor, Henry V.,Chavdarian, Charles G.,Sanders, Edward B.,Bassfield, Ronald L.,Whidby, Jerry F.
, p. 3040 - 3048 (1981)
The stereoselectivity of iodomethylation of nicotine and seven nicotine analogues 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 regioselectively cis to the pyridine ring for all compounds examined.The N/N' and N'cis/N'trans ratios for the nicotinoids were evaluated with regard to (1) the orientation of the N'-methyl group in the free base, (2) conformational properties of the pyridine ring with respect to the pyrrolidine ring, and (3) steric hindrance and buttressing effects on the pyridine nitrogen.The Curtin-Hammett principle and the Winstein-Holness equation are used to analyse reactions.
THE SELECTIVITY IN N-ALKYLATION OF NICOTINE.
Shibagaki, Makoto,Matsushita, Hajime,Shibata, Saizo,Saito, Akira,Tsujino, Yasuko,Kaneko, Hajime
, p. 1641 - 1646 (2007/10/02)
In preference to pyrrolidine, pyridine moiety of nicotine was alkylated by alkyl halides.This preference seemed to result from the difference of steric hinderance around each nitrogen.The reactivity of pyridine moiety was accelerated by the electronic effect of pyrrolidine.The selective alkylation of pyridine appeared to be available for preparation of artificial antigen of nicotine.
