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Volumn 119, Issue 37, 1997, Pages 8718-8719

The first polycondensation through a free radical chain process

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL;

EID: 0030967772     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970165g     Document Type: Article
Times cited : (4)

References (29)
  • 1
    • 33646965165 scopus 로고
    • (a) Endo, T. KobunsM 1986, 35, 272.
    • (1986) KobunsM , vol.35 , pp. 272
    • Endo, T.1
  • 4
    • 33646952560 scopus 로고    scopus 로고
    • ACS Symposium Series 59; American Chemical Society: Washington, DC
    • (a) Saegusa, T., Goethals, E., Eds.; King-Opening Polymerization; ACS Symposium Series 59; American Chemical Society: Washington, DC, 1997.
    • (1997) King-Opening Polymerization
  • 5
    • 33646955377 scopus 로고
    • Elsevier: New York
    • (b) Ivin, K. J., Saegusa, T., Eds.; King-Opening Polymerization; Elsevier: New York, 1984.
    • (1984) King-Opening Polymerization
  • 16
    • 0024305213 scopus 로고
    • Idem. J. Am. Chem. Soc. 1989, 111, 743.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 743
  • 24
    • 33646957221 scopus 로고    scopus 로고
    • note
    • This result was consistent with that of Pasto et al., s' although they reported no details such as yield of the products. Other products: abnormal 1:1 adduct, 1-chloro-3-phenylthiopropene (6%), and 1:2 adduct, 1, 2-bis(phenylthio)-2-chIoropropane (19%).
  • 25
    • 33646953947 scopus 로고    scopus 로고
    • note
    • Reaction conditions: Pyrex filter, toluene, 20 °C, 72 h, PO (2 equiv), and irradiation with a 400 W high-pressure mercury lamp.
  • 26
    • 33646951722 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum may be due to the methylene signal of the polymer unit formed by the terminal addition of thiol to 1.
  • 27
    • 33646962379 scopus 로고    scopus 로고
    • note
    • 1H NMR indicates contamination of a few units different from the 1, 2-diaryIthiopropene unit. This is in good accordance with the model reaction using thiophenol. Rate of terminal carbon attack of thiyl radical (>307o, 8 + 9) is much higher than that of 1 (7%): the product formed by the terminal carbon attack can further react with thiyl radical to yield 8. Therefore, the terminal carbon attack does not result in termination unlike the case of 1: the two main chain structures including a small amount of graft structure can be observed. (Figure Presented)
  • 28
    • 33646951547 scopus 로고    scopus 로고
    • note
    • n 2.09). Unlike the radical addition of thiol to 3-methyI-l , 2-butadiene yielding 1, 2-adduct via the central carbon attack, 14 the polymerization would proceed through initial attack of thiyl radical at the bromo-substituted terminal carbon, because the polymer is suggested to have isopropylidene moiety by the model reaction, in which a different type of 1:2 adduct 11 is selectively formed. (Figure Presented)


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