Design of Thermally Stable Versions of the Burgess Reagent: Stability and Reactivity Study

被引：17
|
作者：
Metcalf, Thomas A.
Simionescu, Razvan
Hudlicky, Tomas [1 ]
机构：
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 10期
基金：
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词：
STEREOSELECTIVE-SYNTHESIS; CHIRAL VERSION; INNER SALT; SULFAMIDES; EPOXIDES; FACILE; ESTERS;
D O I：
10.1021/jo100212n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new versions of the Burgess reagent were synthesized and their thermal stability investigated by NMR. The new reagents exhibited improved reactivity toward epoxides, diols, and vinyl oxiranes as compared with the original version.
引用
收藏
页码：3447 / 3450
页数：4
相关论文
共 50 条
  • [1] Design of a thermally stable small molecule reagent for signal amplification
    Baker, Matthew S.
    Phillips, Scott T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [2] Unexpected reactivity of the burgess reagent with thiols: Synthesis of symmetrical disulfides
    Banfield, Scott C.
    Omori, Alvaro Takeo
    Leisch, Hannes
    Hudlicky, Tomas
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13): : 4989 - 4992
  • [3] Synthesis of N-substituted amidinoheteroles and their reactivity towards Burgess reagent
    Uchiyama, Yosuke
    Kimura, Shinobu
    Kurotaki, Takanori
    Sawamura, Yukihiro
    Kikuchi, Yuichi
    Abe, Shinya
    Runyon, Jason W.
    Dolphin, Joshua S.
    Schinnen, Christoph
    Arduengo, Anthony J., III
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 195 (01) : 3 - 6
  • [4] Synthesis, Structure, and Reactivity of a Thermally Stable Dialkylgermylene
    Suzuki, Fumiaki
    Nishino, Ryohei
    Yukimoto, Mariko
    Sugamata, Koh
    Minoura, Mao
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2020, 93 (02) : 249 - 251
  • [5] Synthesis, structure, and reactivity of a thermally stable dialkylgermylene
    Suzuki, Fumiaki
    Nishino, Ryohei
    Yukimoto, Mariko
    Sugamata, Koh
    Minoura, Mao
    Bulletin of the Chemical Society of Japan, 2020, 93 (02): : 249 - 251
  • [6] Thermally stable small molecule reagent that amplifies signal in water
    Yeung, Kimy
    Schmid, Kyle M.
    Phillips, Scott T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [7] Synthesis, characterization, and reactivity of thermally stable cupric superoxides
    McCollom, Sam
    Weberg, Alexander
    Carroll, Patrick
    Tomson, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [8] Optimal design of thermally stable proteins
    Bannen, Ryan M.
    Suresh, Vanitha
    Phillips, George N., Jr.
    Wright, Stephen J.
    Mitchell, Julie C.
    BIOINFORMATICS, 2008, 24 (20) : 2339 - 2343
  • [9] Computationally guided design of a diazotransfer reagent with high reactivity
    Zheng, Meng-Meng
    Xue, Xiao-Song
    NATURE SYNTHESIS, 2024, 3 (12): : 1455 - 1456
  • [10] Design and synthesis of a thermally stable organic electride
    Redko, MY
    Jackson, JE
    Huang, RH
    Dye, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) : 12416 - 12422
12345