Article
  • Facile Synthesis of Dendritic Benzyl Chlorides from Their Alcohols with Methanesulfonyl Chloride/Et3N
  • Lee JW, Han SC, Kim HJ, Kim JH, Lee UY, Kim BK, Sung SR, Kang HS, Kim JH, Huh DS
  • 덴드리틱 벤질 클로라이드의 효율적인 합성
  • 이재욱, 한승철, 김희주, 김정환, 이언엽, 김병기, 성새름, 강화신, 김지현, 허도성
Abstract
A successful rapid synthesis of dendritic benzyl chlorides from dendritic benzyl alcohols using methanesulfonyl chloride/Et3N as activating agents was described. In this method, each dendritic benzyl chloride can be prepared in one pot: no isolation of intermediate mesylated dendrons is required. The key steps in the syntheses of dendritic benzyl chlorides were the mesylation of the hydroxymethyl group followed by the chlorination by in-situ generated triethylammonium chloride.

덴드리틱 벤질 알코올을 트리에틸아민과 메탄술포닐클로라이드와 반응시켜서, 덴드리틱 벤질 클로라이드의 효율적인 합성이 이루어졌다. 이 반응은 히드록시기의 메실화 반응과 염소화 반응의 2단계 반응으로 이루어지는데, 중간체의 분리없이 한 반응 용기내에서 반응이 진행되는 경제적인 방법이다.

Keywords: benzylic alcohol; chlorination

References
  • 1. Grimsdale AC, Mullen K, Angew. Chem.-Int. Edit., 44, 5592 (2005)
  •  
  • 2. Tomalia DA, Prog. Polym. Sci, 30, 294 (2005)
  •  
  • 3. Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P, Polym. J., 17, 117 (1985)
  •  
  • 4. Tomalia DA, Naylor AM, Goddard III WA, Angew. Chem.-Int. Edit., 29, 138 (1990)
  •  
  • 5. Hawker CJ, Frechet JMJ, J. Am. Chem. Soc., 112, 7638 (1990)
  •  
  • 6. Hawker CJ, Frechet JMJ, J. Chem. Soc. Chem. Commun., 1010 (1990)
  •  
  • 7. Grayson SM, Frechet JMJ, Chem. Rev., 101, 3819 (2001)
  •  
  • 8. Lee JW, Kim BK, Bull. Korean Chem. Soc., 26, 658 (2005)
  •  
  • 9. Lee JW, Kim BK, Jin SH, Bull. Korean Chem. Soc., 26, 715 (2005)
  •  
  • 10. Lee JW, Kim BK, Jin SH, Bull. Korean Chem. Soc., 26, 833 (2005)
  •  
  • 11. Lee JW, Kim BK, Kim JH, Shin WS, Jin SH, Bull. Korean Chem. Soc., 26, 1790 (2005)
  •  
  • 12. Lee JW, Kim BK, Synthesis, 615 (2006)
  •  
  • 13. Lee JW, Kim JH, Kim BK, Shin WS, Jin SH, Tetrahedron, 62, 894 (2006)
  •  
  • 14. Lee JW, Kim BK, Kim JH, Shin WS, Jin SH, J. Org. Chem., 71, 4988 (2006)
  •  
  • 15. Nantalaksakul A, Dasari RR, Ahn TS, Al-Kaysi R, Bardeen CJ, Thayumanavan S, Org. Lett., 8, 2981 (2006)
  •  
  • 16. Forier B, Dehaen W, Tetrahedron, 55, 9829 (1999)
  •  
  • 17. Basso A, Evans B, Pegg N, Bradley M, Chem. Commun., 697 (2001)
  •  
  • 18. Whitmore FC, Karnatz FA, Popkin AH, J. Am. Chem. Soc., 60, 2540 (1938)
  •  
  • 19. Balagurusamy VS, Ungar G, Percec V, Johansson G, J. Am. Chem. Soc., 119(7), 1539 (1997)
  •  
  • 20. Percec V, Cho WD, Mosier PE, Ungar G, Yeardley DJP, J. Am. Chem. Soc., 120(43), 11061 (1998)
  •  
  • 21. Percec V, Cho WD, Ungar G, Yeardley DJP, J. Am. Chem. Soc., 123(7), 1302 (2001)
  •  
  • 22. Percec V, Mitchell CM, Cho WD, Uchida S, Glodde M, Ungar G, Zeng XB, Liu YS, Balagurusamy VSK, Heiney PA, J. Am. Chem. Soc., 126(19), 6078 (2004)
  •  
  • 23. Tanaka M, Higuchi Y, Adachi N, Shibutani Y, Ahmed SA, Kado S, Nakamura M, Kimura K, Tetrahedron, 61, 8159 (2005)
  •  
  • 24. Yamazaki N, Washio I, Shibasaki Y, Ueda M, Org. Lett., 8, 2321 (2006)
  •  
  • 25. Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H, J. Med. Chem., 47, 2853 (2004)
  •  
  • 26. Tanaka K, Katsurada M, Ohno F, Shiga Y, Oda M, Miyagi M, Takehara J, Okano K, J. Org. Chem., 65, 432 (2000)
  •  
  • 27. Mazzini F, Mandoli A, Salvadori P, Netscher T, Rosenau T, Eur. J. Org. Chem., 4864 (2004)
  •  
  • Polymer(Korea) 폴리머
  • Frequency : Bimonthly(odd)
    ISSN 0379-153X(Print)
    ISSN 2234-8077(Online)
    Abbr. Polym. Korea
  • 2022 Impact Factor : 0.4
  • Indexed in SCIE

This Article

  • 2007; 31(5): 417-421

    Published online Sep 25, 2007

  • Received on May 9, 2007
  • Accepted on Jun 29, 2007