A theoretical investigation of the reaction mechanism for hydrogenated furan formation under Prins reaction conditions in trifluoroacetic acid medium

被引：2
作者：
Syrlybaeva, R. R. [1 ]
Vakulin, I. V. [2 ]
Talipov, R. F. [2 ]
机构：
[1] Bashkir State Agr Univ, Informat Technol & Management Fac, Ufa, Russia
[2] Bashkir State Univ, Dept Chem, Ufa 450074, Russia
来源：
REACTION KINETICS MECHANISMS AND CATALYSIS | 2013年 / 109卷 / 02期
关键词：
Prins reaction; Hydrogenated furans; Mechanism; PINACOL SYNTHESIS; CYCLIZATION; TETRAHYDROPYRANS; STEREOSELECTION; MOLECULES;
D O I：
10.1007/s11144-013-0563-4
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The formation mechanism of hydrogenated furans by coupling between terminal alkenes and aldehydes in trifluoroacetic acid medium were investigated by ab initio calculations, the main attention was focused on the study of the rate controlling step. Two possible mechanisms for this reaction involving unsaturated alkoxycarbenium ions or dioxolenium ions as a key intermediate were considered. It was shown that the mechanism of formation of 3-alkylsubstituted hydrogenated furans in trifluoroacetic acid under Prins reaction conditions preferably includes recyclization of 3-(2-hydroxyethyl)-1-trifluoromethyl-2,5-dioxolenium ions.
引用
收藏
页码：301 / 313
页数：13
相关论文
共 31 条
  • [1] Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans
    Cohen, F
    MacMillan, DWC
    Overman, LE
    Romero, A
    [J]. ORGANIC LETTERS, 2001, 3 (08) : 1225 - 1228
  • [2] Gaussian-3 (G3) theory for molecules containing first and second-row atoms
    Curtiss, LA
    Raghavachari, K
    Redfern, PC
    Rassolov, V
    Pople, JA
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1998, 109 (18) : 7764 - 7776
  • [3] Assessment of Gaussian-2 and density functional theories for the computation of enthalpies of formation
    Curtiss, LA
    Raghavachari, K
    Redfern, PC
    Pople, JA
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1997, 106 (03) : 1063 - 1079
  • [4] The correlation consistent composite approach (ccCA):: An alternative to the Gaussian-n methods
    DeYonker, NJ
    Cundari, TR
    Wilson, AK
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2006, 124 (11)
  • [5] Correlated ab initio electronic structure calculations for large molecules
    Friesner, RA
    Murphy, RB
    Beachy, MD
    Ringnalda, MN
    Pollard, WT
    Dunietz, BD
    Cao, YX
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (13) : 1913 - 1928
  • [6] REACTION-PATH FOLLOWING IN MASS-WEIGHTED INTERNAL COORDINATES
    GONZALEZ, C
    SCHLEGEL, HB
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) : 5523 - 5527
  • [7] Tautomerism of hydroxy-pyridazines: the N-oxides
    Greenwood, JR
    Capper, HR
    Allan, RD
    Johnston, GAR
    [J]. THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE, 1997, 419 : 97 - 111
  • [8] Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral
    Hanaki, N
    Link, JT
    MacMillan, DWC
    Overman, LE
    Trankle, WG
    Wurster, JA
    [J]. ORGANIC LETTERS, 2000, 2 (02) : 223 - 226
  • [9] Synthesis of 4-(1-alkenyl)isoquinolines by palladium(II)-catalyzed cyclization/olefination
    Huang, QH
    Larock, RC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 980 - 988
  • [10] Stereoselectivity and regioselectivity in the segment-coupling prins cyclization
    Jaber, JJ
    Mitsui, K
    Rychnovsky, SD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (13) : 4679 - 4686
1234