[3+2] CYCLOADDITION OF N-TERT-BUTYL,α-(4-TRIFLUOROMETHYL)-PHENYLNITRONE WITH METHACROLEIN: THEORETICAL INVESTIGATION

被引：0
|
作者：
Kouchkar, Khaoula [1 ]
Boumedjane, Youcef [1 ]
Hachani, Salah Eddine [2 ]
机构：
[1] Univ Biskra, LMCE Lab, Grp Computat & Pharmaceut Chem, BP 145, Biskra 07000, Algeria
[2] Univ Biskra, Lab Appl Chem LCA, Biskra 07000, Algeria
来源：
CHEMISTRY & CHEMICAL TECHNOLOGY | 2023年 / 17卷 / 03期
关键词：
3+2] cycloaddition; N-tert-butyl; alpha-(4-trifluoromethyl)-phenyl; methacrolein; DFT; regioselectivity; stereoselectivity; DENSITY-FUNCTIONAL THEORY; 1,3-DIPOLAR CYCLOADDITION; AB-INITIO; ONE-STEP; MECHANISM; MOLECULES; DFT; (Z)-C; N-DIPHENYLNITRONE; REGIOSELECTIVITY; ELECTROPHILICITY;
D O I：
10.23939/chcht17.03.518
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
In this scientific contribution, regio-and dia-stereo-selectivity of [3+2] cycloaddition (32CA) of N-tert-butyl,alpha-(4-trifluoromethyl)-phenylnitrone (1) with methacrolein (2) were investigated using DFT method at B3LYP/6-31(d) computational level in gas and dichloro-methane solvent. The molecular electrostatic potential MESP was used to show the most active centers in the examined molecules. Global and local reactivity indices as well as thermodynamic parameters have been calculated to explain the regioselectivity and stereoselectivity for the selected reaction. The possible chemoselective ortho/meta regioselectivity and stereo(endo/exo) isomeric channels were investigated. Our theoretical results give important elucidations for the possible pathways related to the studied 32CA reaction.
引用
收藏
页码：518 / 531
页数：14
相关论文
共 50 条
  • [31] P-TERT-BUTYL-N-[2,4,6-TRI(TERT-BUTYL)PHENYL]-LAMBDA-3-IMINOPHOSPHINE AND P-MESITYL-N-[2,4,6-TRI(TERT-BUTYL)PHENYL]-LAMBDA-3-IMINOPHOSPHINES
    ROMANENKO, VD
    DRAPAILO, AB
    RUBAN, AV
    MARKOVSKII, LN
    ZHURNAL OBSHCHEI KHIMII, 1986, 56 (03): : 714 - 715
  • [32] 4-R-7-Nitrobenzofurazans in [3+2] cycloaddition reactions with N-methylazomethine ylide
    S. Yu. Pechenkin
    A. M. Starosotnikov
    M. A. Bastrakov
    I. V. Glukhov
    S. A. Shevelev
    Russian Chemical Bulletin, 2012, 61 : 74 - 77
  • [33] Thermal intermolecular [3+2] cycloaddition reactions of 4-phthalimido-N-sulfonyltriazoles and substituted arenes
    Wilkerson-Hill, Sidney
    Davies, Huw
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [34] 4-R-7-Nitrobenzofurazans in [3+2] cycloaddition reactions with N-methylazomethine ylide
    Pechenkin, S. Yu
    Starosotnikov, A. M.
    Bastrakov, M. A.
    Glukhov, I. V.
    Shevelev, S. A.
    RUSSIAN CHEMICAL BULLETIN, 2012, 61 (01) : 74 - 77
  • [35] 1-ISOPROPYL-3-TERT BUTYL-1,2-DIAZABUTADIENE-1,3 IN REACTIONS OF [4+2]-CYCLOADDITION
    ZELENIN, KN
    NIKITIN, VA
    ANODINA, NM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1973, (01): : 124 - 128
  • [36] Divulging the various chemical reactivity of trifluoromethyl-4-vinyl-benzene as well as methyl-4-vinyl-benzene in [3+2] cycloaddition reactions
    El Idrissi, Mohammed
    Esme, Asli
    Hakmaoui, Yassine
    Rios-Gutierrez, Mar
    Ouled Aitouna, Anas
    Salah, Mohammed
    Zeroual, Abdellah
    Domingo, Luis R.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2021, 102
  • [37] Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides
    Hou, Jie
    Hao, Wei
    Chen, Ying
    Wang, Zhen
    Yao, Weijun
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9068 - 9077
  • [38] REACTIONS OF A TRIPLET ARYLNITRENIUM ION - LASER FLASH-PHOTOLYSIS AND PRODUCT STUDIES OF N-TERT-BUTYL(2-ACETYL-4-NITROPHENYL)NITRENIUM ION
    SRIVASTAVA, S
    FALVEY, DE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) : 10186 - 10193
  • [39] THE UNEXPECTED FORMATION OF TRANS-BETA-LACTAMS IN THE REACTION OF ALPHA-IMINOESTERS (R-N =C(H)C(=O)OR' WITH DIETHYLZINC - CRYSTAL-STRUCTURE OF TRANS-1-(N-TERT-BUTYL)--3-(N-TERT-BUTYL-N-ETHYLAMINO)-4-METHOXYCARBONYLAZETIDIN-2-ONE
    VANVLIET, MRP
    JASTRZEBSKI, JTBH
    KLAVER, WJ
    GOUBITZ, K
    VANKOTEN, G
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1987, 106 (04): : 132 - 134
  • [40] Synthesis of novel 4,5-diazafluoren-9-one derivatives and theoretical study of 3+2 cycloaddition reactions
    Danac, R
    Constantinescu, M
    Rotaru, A
    Ghirvu, C
    Druta, I
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 41 (06) : 983 - 986
12345