tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis

被引:82
|
作者
Li, Pengfei [1 ]
Jia, Xiaodong [1 ,2 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Anning East Rd 967, Lanzhou 730070, Gansu, Peoples R China
[2] Yangzhou Univ, Sch Chem & Chem Engn, Siwangting Rd 180, Yangzhou 225002, Jiangsu, Peoples R China
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 04期
关键词
tert-butyl nitrite; nitrosation; oximation; diazotization; nitration; oxidation; SANDMEYER TRIFLUOROMETHYLATION; AEROBIC OXYNITRATION; CATALYTIC-SYSTEM; SECONDARY-AMINES; N-NITROSOAMIDES; METAL; ALKENES; CONVERSION; OXIDATION; NITRATION;
D O I
10.1055/s-0036-1589155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
tert-Butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations. Besides its traditional applications in nitrosation and diazotization, its ability to activate molecular oxygen to enable the initiation of radical reactions, including nitration, oximation, oxidation, and so on, has attracted extensively attention in the past decade. This review highlights recent advances in this field to promote further exploration of this versatile compound. 1 Introduction 2 Reactions Involving TBN 2.1 Nitrosation 2.2 Oximation 2.3 Diazotization 2.4 Nitration 2.5 Oxidation 2.6 Other Reactions 3 Conclusion and Perspective
引用
收藏
页码:711 / 722
页数:12
相关论文
共 50 条
  • [31] MICROWAVE-SPECTRUM AND STRUCTURE OF TERT-BUTYL NITRITE
    不详
    NIPPON KAGAKU KAISHI, 1981, (03) : 317 - 320
  • [32] Amide Hydrolysis Reaction Using tert-Butyl Nitrite
    Tao Suyan
    Xiang Zixin
    Bai Junjie
    Wan Xiao
    Wan Xiaobing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 550 - 560
  • [33] TERT-BUTYL FLUOROFORMATE A NEW REAGENT FOR PEPTIDE SYNTHESES
    SCHNABEL, E
    HERZOG, H
    HOFFMANN, P
    KLAUKE, E
    UGI, I
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (05) : 380 - &
  • [34] Bis(dibenzylideneacetone)palladium(0)/tert-Butyl Nitrite-Catalyzed Cyclization of o-Alkynylanilines with tert-Butyl Nitrite: Synthesis and Applications of Indazole 2-Oxides
    Senadi, Gopal Chandru
    Wang, Ji-Qi
    Gore, Babasaheb Sopan
    Wang, Jeh-Jeng
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (16) : 2747 - 2753
  • [35] TEST FOR TERT-BUTYL AND ISOPROPYL ALCOHOLS WITH DENIGES REAGENT
    ROBEY, RF
    ROBERTSON, NC
    ANALYTICAL CHEMISTRY, 1947, 19 (05) : 310 - 311
  • [36] (F-TERT-BUTYL)HYPOCHLORITE - A VERSATILE REAGENT
    GARD, GL
    SHREEVE, JM
    JOURNAL OF FLUORINE CHEMISTRY, 1982, 21 (01) : 53 - 53
  • [37] THE SYNTHESIS OF (+)-TERT-BUTYL AND (-)-TERT-BUTYL NONACTATE FROM L-GLUTAMIC ACID
    BATMANGHERLICH, S
    DAVIDSON, AH
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (20) : 1399 - 1401
  • [38] AN EFFICIENT ONE-STEP SYNTHESIS OF TERT-BUTYL GLYCINATE AND TERT-BUTYL SARCOSINATE
    CAVELIER, F
    ROLLAND, M
    VERDUCCI, J
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (05) : 608 - 610
  • [39] PHOTODISSOCIATION DYNAMICS OF TERT-BUTYL NITRITE (S-2) AND TERT-BUTYL HYDROPEROXIDE AT 248-250 NM
    AUGUST, J
    BROUARD, M
    DOCKER, MP
    MILNE, CJ
    SIMONS, JP
    LAVI, R
    ROSENWAKS, S
    SCHWARTZLAVI, D
    JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (19): : 5485 - 5491
  • [40] A Facile Synthesis of β-Iodonitro Alkenes via Iodonitration of Alkynes with tert-Butyl Nitrite and Iodine
    Fan, Yuanyuan
    Zhou, Bei
    Chen, Kun
    Wang, Bingtao
    Li, Xiaoqing
    Xu, Xiangsheng
    SYNLETT, 2017, 28 (13) : 1657 - 1659