Synthesis of Chiral (R)-4-Hydroxy- and (R)-4-Halogeno[2.2]paracyclophanes and Group Polarizability. Optical Rotation Relationship

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3744-3747

  Cipiciani, Antonio ^a   Fringuelli, Francesco ^a   Mancini, Vittorio ^a   Piermatti, Oriana ^a   Pizzo, Ferdinande ^a   Ruzziconi, Renzo ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001552641     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962142a     Document Type: Article

References (28)

1. (a) Brown, C. J.; Farthing, A. C. Nature (London) 1949, 164, 915.
2. (b) Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691.
3. Vögtle, F.; Neumann, P. Synthesis 1973, 85.
4. See: (a) Vögtle, F. Cyclophane Chemistry, Synthesis, Structure and Reactions; J. Wiley & Sons Ltd.: Chichester, 1993; Chapter 2, pp 71-112. (b) Hopf, H.; Marquard, C. In Strain and its Implications in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer: Dordrecht, 1989; p 297. (c) Staab, H. A.; Knaus, G. H.; Henke, H.-E.; Krieger, C. Chem. Ber. 1983, 116, 2785. (d) Boekelheide, V. Top. Curr. Chem. 1983, 113, 87.
5. See: (a) Vögtle, F. Cyclophane Chemistry, Synthesis, Structure and Reactions; J. Wiley & Sons Ltd.: Chichester, 1993; Chapter 2, pp 71-112. (b) Hopf, H.; Marquard, C. In Strain and its Implications in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer: Dordrecht, 1989; p 297. (c) Staab, H. A.; Knaus, G. H.; Henke, H.-E.; Krieger, C. Chem. Ber. 1983, 116, 2785. (d) Boekelheide, V. Top. Curr. Chem. 1983, 113, 87.
6. See: (a) Vögtle, F. Cyclophane Chemistry, Synthesis, Structure and Reactions; J. Wiley & Sons Ltd.: Chichester, 1993; Chapter 2, pp 71-112. (b) Hopf, H.; Marquard, C. In Strain and its Implications in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer: Dordrecht, 1989; p 297. (c) Staab, H. A.; Knaus, G. H.; Henke, H.-E.; Krieger, C. Chem. Ber. 1983, 116, 2785. (d) Boekelheide, V. Top. Curr. Chem. 1983, 113, 87.
7. See: (a) Vögtle, F. Cyclophane Chemistry, Synthesis, Structure and Reactions; J. Wiley & Sons Ltd.: Chichester, 1993; Chapter 2, pp 71-112. (b) Hopf, H.; Marquard, C. In Strain and its Implications in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer: Dordrecht, 1989; p 297. (c) Staab, H. A.; Knaus, G. H.; Henke, H.-E.; Krieger, C. Chem. Ber. 1983, 116, 2785. (d) Boekelheide, V. Top. Curr. Chem. 1983, 113, 87.
8. (a) Tochtermann, W.; Vagt, U.; Snatzke, G. Chem. Ber. 1985, 118, 1996.
9. (b) Schlögl, K. Top. Curr. Chem. 1984, 125, 27.
10. (c) Falk, H.; Reich-Rohrwig, P.; Schlögl, K. Tetrahedron 1970, 26, 511.
11. (d) Nugent, M. J.; Weigang, O. E., Jr. J. Am. Chem. Soc. 1969, 91, 4556.
12. (e) Falk, H.; Schlögl, K. Angew. Chem., Int. Ed. Engl. 1968, 7, 383.
13. Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289.
14. Beak, P.; Basha, A.; Kokko, B.; Loo, D. J. Am. Chem. Soc. 1986, 108, 6016.
15. The enantiomers of 4-hydroxy[PC] have been resolved by enantioselective gas chromatography, but neither the sign of the specific rotation nor the absolute configuration were assigned (König, W. A.; Gehrcke, B.; Hochmuth, D. H.; Mlynek, C.; Hopf, H. Tetrahedron: Asymmetry 1994, 5, 347).
16. (a) Antonov, D. Y.; Belokon, Y. N.; Ikonnikov, N. S.; Orlova, S. A.; Pisarevsky, A. P.; Raevski, N. I.; Rozenberg, V. I.; Sergeeva, E. V.; Struchkov, Y. T.; Tararov, V. I.; Vorontsov, E. V. J. Chem. Soc., Perkin Trans. 1 1995, 1873.
17. (b) Rozenberg, V. I.; Kharitonov, V.; Antonov, D. Y., Sergeeva, E. V.; Aleshkin, A.; Ikonnikov, N. S.; Orlova, S. A.; Belokon, Y. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 91.
18. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York, 1994; p 1084.
19. The enantiomers of 4-F-, 4-Cl-, and 4-Br[PC] were resolved by chiral HPLC (Hopf, H.; Grahn, W.; Barrett, D. G.; Gerdes, A.; Hilmer, J.; Hucker, J.; Okamoto, Y.; Kaida, Y. Chem. Ber. 1990, 123, 841), but neither the sign of the specific rotations nor the absolute configurations were reported.
20. (a) Nakazaki, M.; Yamamoto, K.; Tanaka, S.; Kametani, H. J. Org. Chem. 1977, 42, 287.
21. (b) Delton, M. H.; Cram, D. J. J. Am. Chem. Soc. 1972, 94, 2471.
22. (c) Cram, D. J.; Singer, L. A. J. Am. Chem. Soc. 1963, 85, 1075.
23. The values of -0.0172 and 1.54 for m and n, respectively, have been calculated including the fluorine data in plot a of Figure 1.
24. Reich, H. J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 3534.
25. The process is favored by adding some crystals of (R)-2-enriched camphorsulfonic salt to induce the crystallization.
26. Norcross, B. E.; Becker, D.; Cukier, R. I.; Schultz, R. M. J. Org. Chem. 1967, 32, 220.
27. Takemura, T.; Mori, N. Chem. Lett. 1978, 857.
28. 12