Synthesis of diols using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate)

被引:41
|
作者
Celik, Murat [1 ]
Alp, Cemalettin
Coskun, Betul
Gultekin, M. Serdar
Balci, Metin
机构
[1] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey
[2] Middle E Tech Univ, Dept Chem, TR-06530 Ankara, Turkey
关键词
phenyliodine(III) bis(trifluoroacetate); PIFA; oxidation; rearrangement; 1.2-diols; 1.3-diols;
D O I
10.1016/j.tetlet.2006.03.137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1.2- and 1.3-Bis(trifluoroacetoxy) alcohols are easily obtained from the one-pot reaction of alkenes with phenyliodine(III) bis(trifluoroacetate) (PIFA) in the absence of any additive or catalyst. The products were converted into the corresponding diols by ammonolysis. The use of bicyclic alkenes has shown that rearranged 1,3-diacetoxy alcohols are mostly formed as the major products. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3659 / 3663
页数:5
相关论文
共 50 条
  • [21] PHENYLIODINE(III) BIS[PHTHALIMIDATE] - A NOVEL POLYVALENT IODINE COMPOUND
    HADJIARAPOGLOU, L
    SPYROUDIS, S
    VARVOGLIS, A
    SYNTHESIS-STUTTGART, 1983, (03): : 207 - 208
  • [22] Novel and efficient synthesis of sulfur-containing heterocycles using a hypervalent iodine(III) reagent
    Kita, Y
    Egi, M
    Ohtsubo, M
    Saiki, T
    Takada, T
    Tohma, H
    CHEMICAL COMMUNICATIONS, 1996, (19) : 2225 - 2226
  • [23] An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent
    Ghosh, Harisadhan
    Yella, Ramesh
    Ali, Abdur Rezzak
    Sahoo, Santosh K.
    Patel, Bhisma K.
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2407 - 2410
  • [24] Synthesis of nitrogen heterocycles by intramolecular cyclization of alkenyl N-acylaminophthalimides using phenyliodine(III) bis(trifluoroacetate) (PIFA)
    Tsukamoto, Masato
    Murata, Kousuke
    Sakamoto, Takeshi
    Saito, Setsuo
    Kikugawa, Yasuo
    HETEROCYCLES, 2008, 75 (05) : 1133 - 1149
  • [25] Regioselective synthesis of isoxazoles by hypervalent iodine(III) reagent mediated oxidative cyclization
    Jarvi, Melissa
    Rohde, Greg
    Nemykin, Victor
    Zhdankin, Viktor
    Yoshimura, Akira
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [26] Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Promoted Synthesis of Bodipy Dimers Displaying Unusual Redox Properties
    Rihn, Sandra
    Erdem, Mustafa
    De Nicola, Antoinette
    Retailleau, Pascal
    Ziessel, Raymond
    ORGANIC LETTERS, 2011, 13 (08) : 1916 - 1919
  • [27] Oxidative rearrangement of pentaalkoxychalcones with phenyliodine(III) bis(trifluoroacetate) (PIFA):: synthesis of (±)-10-bromopterocarpin and (±)-pterocarpin
    Miki, Y
    Fujita, R
    Matsushita, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16): : 2533 - 2536
  • [28] Direct synthesis of bipyrroles using phenyliodine bis(trifluoroacetate) with bromotrimethylsilane
    Dohi, T
    Morimoto, K
    Maruyama, A
    Kita, Y
    ORGANIC LETTERS, 2006, 8 (10) : 2007 - 2010
  • [29] Hypervalent iodine in synthesis.: 61.: Regeneration of carbonyl function from carbonyl derivatives using polymer-supported phenyliodine bis(trifluoroacetate)
    Chen, DJ
    Cheng, DP
    Chen, ZC
    SYNTHETIC COMMUNICATIONS, 2001, 31 (24) : 3847 - 3850
  • [30] A New Synthetic Protocol for the Preparation of Carbodiimides Using a Hypervalent Iodine(III) Reagent
    Zhu, Chenjie
    Xu, Dan
    Wei, Yunyang
    SYNTHESIS-STUTTGART, 2011, (05): : 711 - 714