Prologue: Atropisomerism

Jay S. Siegel received his Ph.D. from Princeton (1985), was a Swiss Universities Fellow at ETH Zurich (1983-4), and NSF–CNRS postdoctoral fellow at the University of Louis Pasteur in Strasbourg (1985-6). He began as Assistant Professor of Chemistry (1986) at UCSD, was promoted to Associate Professor (1992) and Full Professor (1996). In 2003, he was appointed as Professor and co-director of the Organic chemistry institute of the University of Zurich (UZH) and Director of its laboratory for process chemistry research (LPF). He served as Dean of Studies and Head of the Research Council for the Faculty of Sciences at UZH. He moved to Tianjin University in 2013 as dean, and joined the Schools of Pharmaceutical and Life Sciences into a new Health Science Platform. His research is in the area of Stereochemistry and Physical Organic Chemistry.

• References and Notes

• 1 https://www.greekmythology.com/Other_Gods/The_Fates/the_ fates.html

Classical:
• 2a Oki M. Top. Stereochem. 1983; 14: 1
• 2b Kuhn R. Molekulare Asymmetrie. In Stereochemie. Freudenberg K. Franz-Deutike Verlag; Leipzig-Wien: 1933
• 2c Wang Y. Alleman O. Vanthuyne N. Linden A. Baldridge KK. Siegel JS. Angew. Chem. Int. Ed. 2018; 57: 6470
• 3a Kekulé FA. Justus Liebigs Ann. Chem. 1866; 137: 158
• 3b Kekulé FA. Justus Liebigs Ann. Chem. 1872; 163: 77
• 4 van’t Hoff JH. Arch. Neerl. Sci. Exactes Nat. 1874; 9: 445
• 5 For and interesting discussion see: Montaudo G. Gazz. Chim. It. 1997; 127: 837
• 6a Koerner W. Giorn. Sci. Nat. Econom. 1869; 5: 212
• 6b For a superb discussion of Koerner’s proof, see: McBride JM. J. Am. Chem. Soc. 1980; 102: 4134
• 7a Paterno E. Giorn. Sci. Palermo 1869; 3: 117

compare:
• 7b Paterno E. Gazz. Chim. It. 1919; 49: 341
• 8a A humorous account of this is presented in: Heilbronner E. Dunitz JD. Reflections on Symmetry in Chemistry and Elsewhere. Helvetica Chimica Acta and VCH; Basel and Weinheim: 1993: 154
• 8b Wilcox Jr. DH. Greenbaum FR. J. Chem. Educ. 1965; 42: 266
• 9 van’t Hoff JH. Die Lagerung der Atome in Raume. Vieweg und Sohn; Braunschweig: 1877
• 10 For more historical context see: Ramberg PJ. HYLE: Int. J. Phil. Chem. 2000; 6: 35
• 11 Mills WH. Nixon IG. J. Chem. Soc. 1930; 2510
• 12a Pauling L. J. Am. Chem. Soc. 1931; 53: 1367
• 12b Pauling L. J. Am. Chem. Soc. 1932; 54: 988
• 13 Wheland GW. Advanced Organic Chemistry. 3rd ed. John Wiley & Sons Inc; New York: 1960
• 14 Sutton LE. Pauling L. Trans. Faraday Soc. 1935; 31: 939
• 15 Siegel JS. Angew. Chem. Int. Ed. 1994; 33: 1721
• 16 Christie GH. Kehner J. J. Chem. Soc. 1922; 121: 614
• 17 Kemp JD. Pitzer KS. J. Chem. Phys. 1936; 4: 749
• 18 Pitzer KS. J. Chem. Phys. 1937; 5: 473
• 19a Nambu M. Baldridge KK. Mohler D. Hardcastle K. Siegel JS. J. Am. Chem. Soc. 1993; 115: 6138
• 19b Kilway KV. Siegel JS. J. Am. Chem. Soc. 1991; 113: 2332
• 19c Baldridge KK. Siegel JS. J. Phys. Chem. 1996; 100: 6111
• 20 Cahn RS. Ingold C. Prelog V. Angew. Chem. Int. Ed. 1966; 5: 385
• 21 Cahn RS. Ingold CK. Prelog V. Experientia 1956; 12: 81
• 22 Mislow K. Siegel JS. J. Am. Chem. Soc. 1984; 106: 3319
• 23 Prelog V. Helmchen G. Angew. Chem. Int. Ed. 1982; 21: 567
• 24 See: https://cen.acs.org/sections/quizzes/atropisomers.html
• 25 See the critique of pseudo-asymmetry in: Mislow K., Siegel J. S.; J. Am. Chem. Soc.; 1984, 106: 3319
• 26 Canfield PJ. Blake LM. Cai Z.-L. Luck IJ. Krausz E. Kobayashi R. Reimers JR. Crossley M. J. Nat. Chem. 2018; 10: 615