Mechanism of 1,3-dipolar cycloaddition reactions of indan-1-one enamines with aryl nitrile oxide: a DFT analysis

被引：0
|
作者：
Khojastehnezhad, Amir [1 ]
Eshghi, Hossein [2 ]
Moeinpour, Farid [3 ]
Raoufi, Arastou [4 ]
机构：
[1] Islamic Azad Univ, Mashhad Branch, Young Researchers & Elite Club, Mashhad, Iran
[2] Ferdowsi Univ Mashhad, Dept Chem, Fac Sci, Mashhad, Iran
[3] Islamic Azad Univ, Bandar Abbas Branch, Dept Chem, Bandar Abbas 7915893144, Iran
[4] Islamic Azad Univ, Mashhad Branch, Dept Chem, Mashhad, Iran
来源：
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2016年 / 13卷 / 09期
关键词：
Regioselectivity; 3+2] Cycloaddition; Aryl nitrile oxide; DFT reactivity indices; DENSITY-FUNCTIONAL THEORY; THEORETICAL-ANALYSIS; REGIOSELECTIVITY; ISOXAZOLINES; REACTIVITY; 1,2,4-OXADIAZOLES; DIPOLAROPHILES; NITRILIMINES; OPTIMIZATION; REPLACEMENTS;
D O I：
10.1007/s13738-016-0879-x
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The mechanism (regioselectivity) of [3+2] cycloaddition reaction of indan-1-one enamines (1ad-1ce) with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous one-step mechanism with a nonpolar character. Theoretical data are in good agreement with the experimental results.
引用
收藏
页码：1629 / 1634
页数：6
相关论文
共 50 条
  • [1] Mechanism of 1,3-dipolar cycloaddition reactions of indan-1-one enamines with aryl nitrile oxide: a DFT analysis
    Amir Khojastehnezhad
    Hossein Eshghi
    Farid Moeinpour
    Arastou Raoufi
    Journal of the Iranian Chemical Society, 2016, 13 : 1629 - 1634
  • [2] 1,3-Dipolar Cycloaddition Reactions of Indan-1-one Enamines across Arylnitrile Oxides Leading to Novel Cyclic Isoxazoline Derivatives
    Jelizi, Hanene
    Wannassi, Nadia
    Rammah, Mohamed El Baker
    Ciamala, Kabula
    Knorr, Michael
    Rousselin, Yoann
    Kubicki, Marek M.
    Strohmann, Carsten
    Enescu, Mironel
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (02) : 383 - 391
  • [3] Mechanism and regioselectivity of 1,3-dipolar cycloaddition reactions of bicyclic monoterpenes with aryl and heteroaryl nitrile oxides: a DFT study
    Eshghi, Hossein
    Khojastehnezhad, Amir
    Moeinpour, Farid
    Bakavoli, Mehdi
    CANADIAN JOURNAL OF CHEMISTRY, 2015, 93 (07) : 749 - 753
  • [4] Porphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions with nitrile oxide
    Liu, XG
    Feng, YQ
    Chen, X
    Li, F
    Li, XG
    SYNLETT, 2005, (06) : 1030 - 1032
  • [5] Spiro Isoxazolines via Nitrile Oxide 1,3-Dipolar Cycloaddition Reactions
    Savage, G. Paul
    CURRENT ORGANIC CHEMISTRY, 2010, 14 (14) : 1478 - 1499
  • [6] 1,3-DIPOLAR CYCLOADDITION OF DIPHENYLNITRONE TO ENAMINES
    NOMURA, Y
    FURUSAKI, F
    TAKEUCHI, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (07) : 1740 - +
  • [7] 1,3-DIPOLAR CYCLOADDITION OF CARBON DISULFIDE TO A NITRILE OXIDE
    FOYE, WO
    KAUFFMAN, JM
    JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07): : 2417 - &
  • [8] The 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides in Water Media
    Plumet, Joaquin
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (22) : 2683 - 2707
  • [9] STUDIES OF ENAMINES .1. 1,3-DIPOLAR CYCLOADDITION OF NITRONES TO ENAMINES
    TSUGE, O
    TASHIRO, M
    NISHIHAR.Y
    NIPPON KAGAKU ZASSHI, 1971, 92 (01): : 72 - &
  • [10] 1,3-DIPOLAR CYCLOADDITION OF ARYL NITRILE OXIDES TO 5-SPIROSTENES
    SIDDIQUI, AU
    SIDDIQUI, AH
    RAMAIAH, TS
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1992, 69 (05) : 282 - 284
12345