The road to chiral amplification in polymers originated in Italy

Chirality

Volumn 9, Issue 5-6, 1997, Pages 424-427

  Green, Mark M ^a   Jha, Salil K ^a  

^a POLYTECHNIC UNIVERSITY   (United States)

Author keywords

Chiral amplification; Italy; Polymers

Indexed keywords

ISOCYANIC ACID DERIVATIVE; POLYMER; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; CRYSTALLIZATION; ENANTIOMER; ITALY; POLYMERIZATION; PRIORITY JOURNAL; RACEMIC MIXTURE; SOLID STATE; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030961044     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<424::AID-CHIR4>3.0.CO;2-5     Document Type: Article

References (22)

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2. See also: Bailey, W.J., Yates, E.T., Polymers III. Synthesis of optically active stereoregular polyolefins, J. Org. Chem. 25:1800, 1960.
3. Pino, P., Lorenzi, G.P. Optically active vinyl polymers II. The optical activity of isotactic and block polymers of optically active alpha-olefins in dilute hydrocarbon solvents. J. Am. Chem. Soc. 82:4745, 1960.
4. For a later summary see: Pino, P. Optically active addition polymers. Adv. Polym. Sci. 4:393-456, 1965.
5. Pino, P., Carlini, C., Chielinni, E., Ciardelli, F., Salvadori, P. Dissymetrically perturbed aromatic chromophore in stereoregular copolymers of (R)-3,7-dimethyl-1-octene with styrene. J. Am. Chem. Soc. 90:5025-5027, 1968.
6. For a different approach to this question see: Basssi, I.W., Bonsignori, O., Lorenzi, G.P., Pino, P., Corradini, P., Temussi, P.A. Structure and optical activity of a crystalline modification of isotactic poly-(S)-4-methyl-1-hexene. J. Polym. Sci. Part A-2, 9:193-208, 1971.
7. For an excellent review on the stereochemistry of linear polymers including discussion of such calculations see pages 56-58: Farina, M. The stereochemistry of linear macromolecules. Topics Stereochem. 17;1-111, 1987.
8. See also: Allegra, G., Corradini, P., Ganis, P. A model of the chain conformation of an isotactic vinyl polymer, having optically active side groups. Makromol. Chemie. 90:60-65, 1966.
9. Carlini, C., Ciardelli, F., Pino, P. Optical activity and conformation in solution of stereoregular copolymers of (S)-4-methyl-1-hexene and with 4-methyl-1-pentene. Makromol. Chemie. 119:244-248, 1968.
10. Luisi, P.L., Pino, P. Conformational properties of optically active poly-alpha-olefines in solution. J. Phys. Chem. 72:2400-2405, 1968.
11. Pino, P., Ciardelli, F., Montagnoli, G., Pieroni, O. On the relationship between monomer optical purity and polymer rotatory power in some linear poly-alpha-olefines. J. Polym. Sci. Polymer Lett. 5:307-311, 1967.
12. Pino, P. The control of main chain conformation in vinyl- and related polymers. Polymer Preprints (ACS) 30(2):433-434, 1989;
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15. Klesper, E. Chirality in vinyl polymers, IUPAC International Symposium on Macromolecules (SIM), Rio de Janeiro, 1974, Paper B-1, 3, 77.
16. Green, M.M., Peterson, N.C., Sato, T., Teramoto, A., Cook, R., Lifson, S. A helical polymer with a cooperative response to chiral information. Science 268:1860, 1995.
17. Green, M.M., Andreola, C., Munoz, B., Reidy, M.P., Zero, K. Macromolecular stereochemistry: A cooperative deuterium isotope effect leading to a large optical rotation. J. Am. Chem. Soc. 110:4063-4065, 1988;
18. Green, M.M., Reidy, M.P., Johnson, R.D., Darling, G., O'Leary, D.J., Wilson, G. Macromolecular stereochemistry: The out-of-proportion influence of optically active comonomers on the conformational characteristics of polyisocyanates. The sergeants and soldiers experiment, J. Am. Chem. Soc. 111:6452-6454, 1989;
19. Green, M.M., Garetz, BA, Munoz, B., Chang, H., Hoke, S., Cooks, R.G. Majority rules in the copolymerization of mirror image isomers, J. Am. Chem. Soc. 117:4181-4182, 1995.
20. Lifson, S., Andreola, C., Peterson, N.C., Green, M.M. Macromolecular stereochemistry: Helical sense preference in optically active polyisocyanates. Amplification of a conformational equilibrium deuterium isotope effect J. Am. Chem. Soc. 111:8850-8858, 1989;
21. Selinger, J.V., Selinger, R.L.B. Theory of chiral order in random copolymers, Phys. Rev. Lett 76:58-61, 1996.
22. In preparation for Chirality in honor of the Professor Kurt Mislow for the "Chirality Medal Award."