New Cyano-Group-Containing 1,3-Oxaselenoles: Nucleophilic Substitution of a Cyano Group with Rearrangement

被引：1
|
作者：
Kachanov, Andrey V. [1 ]
Zamaraev, Andrey V. [2 ]
Gerasimenko, Andrey V. [3 ]
Maslov, Konstantin V. [1 ]
Slabko, Oleg Yu. [1 ]
Kaminskii, Vladimir A. [1 ]
机构：
[1] Far Eastern Fed Univ, Sch Nat Sci, Sukhanov Str 8, Vladivostok 690950, Russia
[2] Russian Acad Sci, Far East Branch, GB Elyakov Pacific Inst Bioorgan Chem, Prospect 100 Let Vladivostoku 159, Vladivostok 690022, Russia
[3] Russian Acad Sci, Far East Branch, Inst Chem, Prospect 100 Let Vladivostoku 159, Vladivostok 690022, Russia
来源：
SYNLETT | 2018年 / 29卷 / 15期
关键词：
aroylacetonitriles; selenium oxide; oxaselenoles; nucleophilic substitution; rearrangement; SELENIUM DIOXIDE; MALONONITRILE; DERIVATIVES; OXIDATION; YLIDES; ROUTE;
D O I：
10.1055/s-0037-1609939
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New cyano-group-containing 1,3-oxaselenoles were obtained by the treatment of aroylacetonitriles with selenium(IV) oxide. The resulting products were shown to react with ammonia, hydrazine, or primary amines; this reaction was accompanied by aryl rearrangement.
引用
收藏
页码：2035 / 2038
页数：4
相关论文
共 50 条
  • [1] REACTIONS OF POTASSIUM TRIPHENYLCYANOBORATE WITH CYANO GROUP AS NUCLEOPHILIC CENTRE
    BREHM, E
    HAAG, A
    HESSE, G
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1970, 737 : 80 - &
  • [2] Ferroelectric liquid crystals containing the cyano group
    Kaspar, M
    Sverenyak, H
    Hamplova, V
    Pakhomov, SA
    Glogarova, M
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS SCIENCE AND TECHNOLOGY SECTION A-MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1995, 260 : 241 - 246
  • [3] ORGANOSILICON COMPOUNDS CONTAINING A CYANO-GROUP
    VDOVIN, VM
    PETROV, AD
    RUSSIAN CHEMICAL REVIEWS, 1962, 31 (07): : 393 - 408
  • [4] 1,3-phosphorus zwitterions with cyano-group at anion center
    Gololobov, Yuri G.
    Gololobov, Mikhail Y.
    COMPTES RENDUS CHIMIE, 2010, 13 (8-9) : 900 - 911
  • [5] Cu2+-promoted nucleophilic addition of pyrazole to cyano group
    Zheng, Ling-Ling
    Wang, Jiong-Fei
    Wang, Jing
    Zhou, Ai-Ju
    Liao, Chun-Xian
    Hu, Sheng
    INORGANICA CHIMICA ACTA, 2020, 501
  • [6] Chemo-divergent Cyano Group Migration: Involving Elimination and Substitution of the Key α-Thianthrenium Cyano Species
    Li, Bo
    Xing, Donghui
    Li, Xiaohong
    Chang, Shunqin
    Jiang, Huanfeng
    Huang, Liangbin
    ORGANIC LETTERS, 2023, 25 (36) : 6633 - 6637
  • [7] Unusual "substitution" of carbonyl functional group by cyano group in position 3 of coumarin system
    Nemeryuk, MP
    Dimitrova, VD
    Sedov, AL
    Traven, VF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (10): : 1417 - 1418
  • [8] ELECTRON-TRANSFER SUBSTITUTION-REACTIONS - FACILITATION BY THE CYANO GROUP
    KORNBLUM, N
    FIFOLT, MJ
    TETRAHEDRON, 1989, 45 (05) : 1311 - 1322
  • [9] Synthesis of fullerene containing cyano group and formation of the metal complexes
    Tamura, T
    Kikuchi, K
    Takeoka, Y
    Rikukawa, M
    SYNTHETIC METALS, 2003, 135 (1-3) : 739 - 740
  • [10] Synthesis of poly(phenylacetylenes) containing polar cyano group.
    Kong, XX
    Wan, XH
    Feng, XD
    Tang, BZ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 203 - PMSE
12345