[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
  • [21] Novel azaandrostane derivatives for the synthesis of 17β-(N-tert-butyl carbamoyl)-4-aza-5α-androst-1-ene-3-one
    Rao, Divvela V. N. Srinivasa
    Trinadhachari, Ganala Naga
    Prabahar, Koilpillai Joseph
    Dandala, Ramesh
    Sivakumaran, Meenakshisundaram
    Naidu, Andra
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (03) : 663 - 667
  • [22] The transformation of 2,6-di-tert-butyl-4-(alkylamino)methylphenols to N,N-bis(3,5-di-tert-butyl-4-hydroxylbenzyl)-N-alkylamines
    Zeng, Tao
    Chen, Ligong
    Li, Jiangsheng
    Zhang, Yuecheng
    Deng, Yi
    JOURNAL OF CHEMICAL RESEARCH-S, 2006, (12): : 794 - 796
  • [23] Theoretical investigation of the regio-, enantio-, and stereo-selectivities of the (3+2) cycloaddition reactions of N-vinylindoles with nitrones and nitrile oxides
    Samba, Wisdom Kwaku
    Amoah, Anthony
    Tia, Richard
    Adei, Evans
    THEORETICAL CHEMISTRY ACCOUNTS, 2021, 140 (11)
  • [24] The mechanism, the chemoselectivity and the regioselectivity of the 1-benzyl-4-ethynyl-1H-[1,2,3]triazole and 1-azidomethyl-4-tert-butyl-benzene in [3+2] cycloaddition reactions: a DFT study
    El Haib, A.
    El Ajlaoui, R.
    El Idrissi, M.
    Moumou, M.
    Abouricha, S.
    Zeroual, A.
    Benharref, A.
    El Hajbi, A.
    MOROCCAN JOURNAL OF CHEMISTRY, 2018, 6 (01): : 14 - 21
  • [25] Catalytic Asymmetric Synthesis of Vicinally Bis(trifluoromethyl)-Substituted Molecules via Normal [3+2] Cycloaddition of N-2,2,2-Trifluoroethyl Benzothiophene Ketimines and β-Trifluoromethyl Enones
    Zhao, Jian-Qiang
    Zhang, Xue-Man
    He, Yu-Ying
    Peng, Qiao-Qiao
    Rao, Han-Wen
    Zhang, Yan-Ping
    Wang, Zhen-Hua
    You, Yong
    Yuan, Wei-Cheng
    ORGANIC LETTERS, 2023, 25 (44) : 8027 - 8032
  • [26] Effect of iminic nitrogen substituents on [4+2] versus [3+2] cycloaddition pathways in reactions of nitrosoalkenes with simple acyclic imines: an experimental and theoretical investigation
    Marwaha, A
    Bharatam, PV
    Mahajan, MP
    TETRAHEDRON LETTERS, 2005, 46 (47) : 8253 - 8256
  • [27] A theoretical investigation of the regio- and stereoselectivities of the [3+2] cycloaddition reaction between ethyl vinyl ether and substituted α-alkoxynitrones
    Houiene, Zahia
    Gharbi, Rim
    Manachou, Marwa
    Belkhiri, Lotfi
    THEORETICAL CHEMISTRY ACCOUNTS, 2022, 141 (05)
  • [28] Mechanistic study of N-t-butyl nitrone and cyanoacetylene [3+2] cycloaddition: a combined DFT, docking, and ADMET approach
    Salih, Raad Nasrullah
    Mohammad-Salim, Haydar
    Algso, Muheb
    MONATSHEFTE FUR CHEMIE, 2025, 156 (04): : 443 - 456
  • [29] Organocatalytic Asymmetric [3+2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines with β-Trifluoromethyl Electron Deficient Alkenes: Access to Vicinally Bis(trifluoromethyl)-Substituted 3,2′-Pyrrolidinyl Spirooxindoles
    You, Yong
    Lu, Wen-Ya
    Wang, Zhen-Hua
    Chen, Yong-Zheng
    Xu, Xiao-Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    ORGANIC LETTERS, 2018, 20 (15) : 4453 - 4457
  • [30] [1+4]-cycloaddition of a stable silylene to 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene
    Clendenning, SB
    Gehrhus, B
    Hitchcock, PB
    Nixon, JF
    CHEMICAL COMMUNICATIONS, 1999, (24) : 2451 - 2452
12345