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Volumn 32, Issue 23, 1999, Pages 7732-7736

Synthesis of highly optically active polysulfoxides by asymmetric oxidation of polysulfides

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CHLORINE COMPOUNDS; GLASS TRANSITION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL MATERIALS; OXIDATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 0033313564     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma981870s     Document Type: Article
Times cited : (20)

References (46)
  • 2
    • 0001428657 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, Chapter 3
    • For reviews, see: (a) Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6; Chapter 3, pp 148-170.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 148-170
    • Solladié, G.1
  • 5
    • 50549178839 scopus 로고
    • Synthesis of chiral sulfoxides by nucleophilic substitution of chiral menthylsulfinate ester with Grignard reagents (Andersen synthesis): (a) Andersen, K. K. Tetrahedron Lett. 1962, 93.
    • (1962) Tetrahedron Lett. , pp. 93
    • Andersen, K.K.1
  • 7
    • 0001757020 scopus 로고
    • (c) Drabowicz, J.; Bujnicki, B.; Mikolajczyk, M. J. Org. Chem. 1982, 47, 3325. Though Andersen synthesis proceeds with complete inversion of chirality at the sulfur atom to give a homochiral sulfoxide, it has some defects such as limitation of substrates, and it is not suitable for polymer synthesis.
    • (1982) J. Org. Chem. , vol.47 , pp. 3325
    • Drabowicz, J.1    Bujnicki, B.2    Mikolajczyk, M.3
  • 8
    • 33751392007 scopus 로고
    • Other methods to prepare chiral sulfoxides by the nucleophilic substitution at the sulfur atom. Using diacetone-D-glucose: (a) Fernández, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789-6796. From a chiral sulfite:
    • (1992) J. Org. Chem. , vol.57 , pp. 6789-6796
    • Fernández, I.1    Khiar, N.2    Llera, J.M.3    Alcudia, F.4
  • 35
    • 0342763378 scopus 로고
    • An example of the synthesis of the liquid crystalline polymers having sulfoxide groups with low enantiomeric excess (25% ee) in the main chain by polymer reaction: (a) Angeloni, A. S.; Laus, M.; Caretti, D.; Chiellini, E.; Galli, G. Makromol. Chem. 1990, 191, 2787-2793. Examples of the polymerization of optically active vinyl sulfoxides:
    • (1990) Makromol. Chem. , vol.191 , pp. 2787-2793
    • Angeloni, A.S.1    Laus, M.2    Caretti, D.3    Chiellini, E.4    Galli, G.5
  • 39
    • 0031647058 scopus 로고    scopus 로고
    • An example of the synthesis of stereoregular poly(carbosilane) by using an optically active silane as a monomer: Kawakami, Y.; Takeyama, K.; Komuro, K.; Ooi, O. Macromolecules 1998, 31, 551-553.
    • (1998) Macromolecules , vol.31 , pp. 551-553
    • Kawakami, Y.1    Takeyama, K.2    Komuro, K.3    Ooi, O.4
  • 41
    • 0342763370 scopus 로고    scopus 로고
    • note
    • Number-average molecular weight of the polymer 2 was estimated from the ratio of an integral of terminal vinyl protons with that of main-chain methylene protons.
  • 42
    • 0343633697 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum.
  • 44
    • 0342763368 scopus 로고    scopus 로고
    • 3]) and chiral amide shift reagent ((R)-(-)-N-(3,5-dinitrobenzoyl)-a-methylbenzylamine) were used for estimating enantiomeric excess of the polysulfoxides. However, the peak separation was hardly observed probably due to broadening of the peaks, (a) Reference 5j
    • 3]) and chiral amide shift reagent ((R)-(-)-N-(3,5-dinitrobenzoyl)-a-methylbenzylamine) were used for estimating enantiomeric excess of the polysulfoxides. However, the peak separation was hardly observed probably due to broadening of the peaks, (a) Reference 5j.
  • 46
    • 0343633696 scopus 로고    scopus 로고
    • note
    • 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.