Synthesis of O-tert-Butyl-N,N-disubstituted Hydroxylamines by N-O Bond Formation

被引：10
|
作者：
Hill, Jarvis [1 ,2 ]
Crich, David [1 ,2 ,3 ]
机构：
[1] Univ Georgia, Dept Pharmaceut & Biomed Sci, Athens, GA 30602 USA
[2] Univ Georgia, Dept Chem, Athens, GA 30602 USA
[3] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
关键词：
TERT-BUTYL PEROXYBENZOATE; STEPWISE REDUCTION; LITHIUM-SALTS; SUBSTITUTION; HYDROLYSIS;
D O I：
10.1021/acs.orglett.1c02215
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of magnesium amides with tert-butyl 2,6-dimethyl perbenzoate in tetrahydrofuran at 0 degrees C provides a method for the synthesis O-tert-butyl-N,N-disubstituted hydroxyl-amines by direct N-O bond formation with a broad functional group tolerance. Less sterically hindered magnesium amides require ortho,ortho-disubstitution on the perester electrophile component, whereas sterically encumbered magnesium amides perform comparably with either tert-butyl perbenzoate or tert-butyl 2,6-dimethyl perbenzoate. A reaction mechanism is presented to account for the observed reactivity.
引用
收藏
页码：6396 / 6400
页数：5
相关论文
共 50 条
  • [1] Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines
    Dhanju, Sandeep
    Crich, David
    ORGANIC LETTERS, 2016, 18 (08) : 1820 - 1823
  • [2] Diversity-Oriented Synthesis of N,N,O-Trisubstituted Hydroxylamines from Alcohols and Amines by N-O Bond Formation
    Hill, Jarvis
    Hettikankanarnalage, Asiri A.
    Crich, David
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (35) : 14820 - 14825
  • [3] O-Trifluoromethylation of N,N-Disubstituted Hydroxylamines with Hypervalent Iodine Reagents
    Matousek, Vaclav
    Pietrasiak, Ewa
    Sigrist, Lukas
    Czarniecki, Barbara
    Togni, Antonio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) : 3087 - 3092
  • [4] The action of thiocyanogen upon O,N-disubstituted hydroxylamines and primary amines
    Jones, LW
    Fleck, EE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1928, 50 : 2018 - 2028
  • [5] POLYMERIZATION OF STYRENE IN THE PRESENCE OF N,N-DISUBSTITUTED HYDROXYLAMINES
    HRIVIK, A
    BENISKA, J
    HUDECOVA, E
    CHEMICKE ZVESTI, 1983, 37 (04): : 503 - 509
  • [6] Cleavage of the N-O bond in substituted hydroxylamines under basic conditions
    Nikitin, KV
    Andryukhova, NP
    MENDELEEV COMMUNICATIONS, 2000, (01) : 32 - 33
  • [7] Rhodium mediated N-O bond formation
    Burke, HM
    Gallagher, JF
    Indelli, MT
    Scandola, F
    Vos, JG
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2002, (04) : 846 - 849
  • [8] N-O BOND FISSION AS THE MECHANISM OF AQUEOUS DEGRADATION OF N-PEPTIDYL-O-PARA-NITROBENZOYL HYDROXYLAMINES
    DEMUTH, HU
    FISCHER, G
    BARTH, A
    SCHOWEN, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 194 - ORGN
  • [9] Synthesis of N,N-disubstituted (Z)-O-methylnicotinamide oximes
    Martsynkevich, A. M.
    Zakharychev, V. V.
    Sharanina, N. I.
    RUSSIAN CHEMICAL BULLETIN, 2011, 60 (03) : 521 - 525
  • [10] Synthesis of N,N-disubstituted (Z)-O-methylnicotinamide oximes
    A. M. Martsynkevich
    V. V. Zakharychev
    N. I. Sharanina
    Russian Chemical Bulletin, 2011, 60 : 521 - 525
12345