Preparation of polyacetylenes bearing an amino group and their application to chirality assignment of carboxylic acids by circular dichroism

Chirality

Volumn 9, Issue 5-6, 1997, Pages 593-600

  Yashima, Eiji ^a   Maeda, Yukio ^a   Matsushima, Teruyuki ^a   Okamato, Yoshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Acid base; Chiral discrimination; Circular di chroism; Helix; Induced circular dichroism; Polyphenylacetylene; Rhodium catalyst

Indexed keywords

ACETONITRILE; CARBOXYLIC ACID DERIVATIVE; CHLOROFORM; DIMETHYL SULFOXIDE; PHENYLACETIC ACID DERIVATIVE; POLYACETYLENE DERIVATIVE; RHODIUM; SOLVENT; TETRAHYDROFURAN;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; MOLECULAR STABILITY; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0030921906     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:5/6<593::AID-CHIR29>3.0.CO;2-I     Document Type: Article

References (22)

1. Yashima, E., Matsushima, T., Okamoto, Y. Poly((4-carboxylphenyl) acetylene) as a probe for chirality assignment of amines by circular dichroism. J. Am. Chem. Soc. 117:11596-11597, 1995.
2. Yashima, E., Nimura, T., Matsushima, T., Okamoto, Y. Poly((4-dihyroxyborophenyl)-acetylene) as a novel probe for chirality and structural assignments of various kinds of molecules including carbohydrates and steroids by circular dichroism. J. Am. Chem. Soc. 118: 9800-9801, 1996.
3. Yashima, E., Maeda, Y., Okamoto, Y. A stereoregular polyphenylacetylene derivative bearing an amino group as a probe for chirality assignments of acids by circular dichroism. Chem. Lett. 955-956, 1996.
4. Lindgren, M., Lee, H.-S., Yang, W., Tabata, M., Yokota, K. Synthesis of soluble polyphenylacetylenes containing a strong donor function. Polymer 32:1531-1534, 1991.
5. Tabata, M., Namioka, M., Yokota, K. Stereospecific polymerization of mono-substituted acetylene with transition metal complex catalyst 3. Polypyridylacetylene. Polym. Prep. Jpn. 37:1269-1271, 1988.
6. Subramanyam, S., Blumstein, A. Conjugated ionic polyacetylenes. 5. Spontaneous polymerization of 2-ethynylpyridine in a strong acid. Macromolecules 25:4058-4064, 1992.
7. Yashima, E., Huang, S., Matsushima, T., Okamoto, Y. Synthesis and conformational study of optically active poly(phenylacetylene) derivatives bearing a bulky substituent. Macromolecules 28:4184-4193, 1995.
8. Furlani, A., Licoccia, S., Russo, M.V. Rhodium and platinum complexes as catalysts for the polymerization of phenylacetylene. J. Polym. Sci., Part A, Polym. Chem. 24:991-1005, 1986.
9. 1H NMR and UV studies of Rh complexes as a stereoregular polymerization catalyst for phenylacetylenes: Effects of ligands and solvents on its catalyst activity. J. Polym. Sci., Part A, Polym. Chem. 32:1113-1120, 1994.
10. 2. J. Am. Chem. Soc. 116:12131-12132, 1994.
11. Kshimoto, Y., Miyatake, T., Ikariya, T., Noyori, R. An efficient rhodium (I) initiator for stereospecific living polymerization of phenylacetylenes. Macromolecules 28:5054-5055, 1995.
12. Subramanyam, S., Chetan, M.S. Conjugated ionic polyacetylenes. 6. Polymerization of 2-ethynylpyridine triflates. Macromolecules 26: 3212-3217, 1993.
13. Yashima, E., Huang, S., Okamoto, Y. Optically active stereoregular polyphenylacetylene derivative as a novel chiral stationary phase for HPLC. J. Chem. Soc. Chem. Commun. 1811-1812, 1994.
14. Simionescu, C., Dumitrescu, S., Percec, V. Isomeric copolymers of acetylenes. J. Polym. Sci., Polym. Symp. 64:209-227, 1978.
15. Furlani, A., Napoletano, C., V. Russo, M.V., Feast, W.J. Stereoregular polyphenylacetylene. Polym. Bull. 16:311-317, 1986.
16. 1 complexes in reactions with phenylacetylene: Synthesis of stereoregular poly(phenylacetylene). J. Polym. Sci., Part A, Polym. Chem. 27:75-86, 1989.
17. Harada, N., Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry. Mill Valley, CA:University Science Books, 1983.
18. Eliel, E.L, Wilen, S.H. Stereochemistry of Organic Compounds. New York: VCH, 1994, chapter 6, 153-274.
19. Yashima, E., Matsushima, T., Okamoto, Y. Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexation. J. Am. Chem. Soc. 119:1997, in press.
20. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry. Weinheim: VCH, 1990, chapters 3 and 4, 51-120.
21. Izutsu, K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents. Oxford: Blackwell Scientific Publications, 1990.
22. Eliel, E.L, Wilen, S.H. Stereochemistry of Organic Compounds. New York: VCH, 1994, chapter 5, 101-147.