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Resolution of (.+-.)-5-bromonornicotine. Synthesis of (R)- and (S)-nornicotine of high enantiomeric purity

Cite this: J. Org. Chem. 1982, 47, 21, 4165–4167
Publication Date (Print):October 1, 1982
https://doi.org/10.1021/jo00142a032
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    22. G.D. Byrd,, W.S. Caldwell,, B.S. Bhatti,, A. Ravard,, P.A. Crooks,. Determination of Nicotine N-1-Glucuronide, a Quaternary N-Glucuronide Conjugate, in Human Biological Samples. Drug Metabolism and Drug Interactions 2000, 16 (4) , 281-298. https://doi.org/10.1515/DMDI.2000.16.4.281
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    27. Peter A. Crooks. Chemical properties of nicotine and other tobacco-related compounds. 1999, 69-147. https://doi.org/10.1016/B978-044450095-3/50005-X
    28. Peyton Jacob, Gary D. Byrd. Use of gas chromatographic and mass spectrometric techniques for the determination of nicotine and its metabolites. 1999, 191-224. https://doi.org/10.1016/B978-044450095-3/50007-3
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    30. Niranjan M Deo, Peter A Crooks. Regioselective alkylation of N-(diphenylmethylidine)-3-(aminomethyl)pyridine: A simple route to minor tobacco alkaloids and related compounds. Tetrahedron Letters 1996, 37 (8) , 1137-1140. https://doi.org/10.1016/0040-4039(96)00002-0
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    33. H. Nybäck, C. Halldin, A. Åhlin, M. Curvall, L. Eriksson. PET studies of the uptake of (S)- and (R)-[11C]nicotine in the human brain: difficulties in visualizing specific receptor binding in vivo. Psychopharmacology 1994, 115 (1-2) , 31-36. https://doi.org/10.1007/BF02244748
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    35. Linda P. Dwoskin, Susan T. Buxton, Ann L. Jewell, Peter A. Crooks. S (‐)‐Nornicotine Increases Dopamine Release in a Calcium‐Dependent Manner from Superfused Rat Striatal Slices. Journal of Neurochemistry 1993, 60 (6) , 2167-2174. https://doi.org/10.1111/j.1471-4159.1993.tb03502.x
    36. Fuji Yokoi, Tasuku Komiyama, Takashi Ito, Tokishi Hayashi, Masaaki Iio, Toshihiko Hara. Application of carbon-11 labelled nicotine in the measurement of human cerebral blood flow and other physiological parameters. European Journal of Nuclear Medicine 1993, 20 (1) , 46-52. https://doi.org/10.1007/BF02261245
    37. Christer Halldin, Kjell Någren, Carl-Gunnar Swahn, Bengt Långström, Henrik Nybäck. (S)- and (R)-[11C]nicotine and the metabolite ()-[11C]cotinine. preparation, metabolite studies and in vivo distribution in the human brain using PET. International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology 1992, 19 (8) , 871-880. https://doi.org/10.1016/0883-2897(92)90173-V
    38. J. R. Copeland, A. Adem, P. Jacob, A. Nordberg. A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Naunyn-Schmiedeberg's Archives of Pharmacology 1991, 343 (2) , 123-127. https://doi.org/10.1007/BF00168598
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    41. Klaus Bernauer, François Gretillat. Stereoselectivity in Reactions of Metal Complexes. Part XI. 2,6‐Bis(pyrrolidin‐2‐yl)pyridine: Synthesis and resolution of the meso and the optically active isomers. Complex formation with copper(II) ion in aqueous solution. Helvetica Chimica Acta 1989, 72 (3) , 477-481. https://doi.org/10.1002/hlca.19890720309
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