S. Okovytyy
322
51. Omoto K, Fujumoto H (2000) Theoretical study of activation of oxirane by bidentate acids. J
Org Chem 65(8):2464–2471
52. Shibaev AYu, Astrat’eva NV, Tereshchenko GF (1984) Quantum-chemical study of ethylene
oxide amination. Zh Obsh Khim 54(12):2744–2747
53. Lundin A, Panas I, Ahlberg E (2009) Quantum chemical modeling of propene and butene
epoxidation with hydrogen peroxide. J Phys Chem A 113(1):282–290
54. Zheng Y, Zhang J (2010) Interface water catalysis of the epoxide opening. Chem Phys Chem
11(1):65–69
55. Long FA, Pritchard JG (1956) Hydrolysis of substituted ethylene oxides in H 2 O
18
solutions.
J Am Chem Soc 78(12):2663–2667
56. Parker RE, Isaacs MS (1956) Mechanisms of epoxide reactions. Chem Rev 59(4):737–799
57. Pritchard JG, Long FA (1956) Kinetics and mechanism of the acid-catalyzed hydrolysis of
substituted ethylene oxides. J Am Chem Soc 78(12):2667
58. Taft RW (1952) The Dependence of the rate of hydration of isobutene on the acidity function,
H 0 , and the mechanism for olefin hydration in aqueous acids. J Am Chem Soc 74(21):5372–
5376
59. Wohl RA (1974) The Mechanism of the acid-catalized king opening of epoxides. A reinterpretative review. Chimia 28(1):1–5
60. Okovytyy S, Gorb L, Leszczynski J (2001) New insight on the mechanism of 2-oxabicyclobutane fragmentation. A high-level ab initio study. Tetrahedron 57(8):1509–15013
61. Lebedev NN, Guskov KA (1963) Reaction of α-oxides. II. Kinetics of the reactions of ethylene oxides with acetic and monochloroacetic acids. Kinet Katal 4(1):116–127
62. Lebedev NN, Kozlov VM (1966) Kinetics and mechanism of reaction of ethylene oxide and
acids. Zh Obsh Khim 2(2):261–265
63. Kakiuchi H, Tijima T (1980) The ring-opening reactions of propylene oxide with chloroacetic acids. Tetrahedron 36(8):1011–1016
64. Stepanov EG, Podgornova VA, Ustavshchikov BF (1976) Effect of the structure of the carboxylic acid on the reactivity in the reaction with propylene oxide. Osnovn Organ Sintez i
Neftekhimiya 6:29–31
65. Kretova EN, Podgornova VA, Bastrakova ZA, Chagina NT (1984) Zh Fizich Khim
58(11):2885–2887
66. Kretova EN (1985) Calculation of the electronic structure of protonated ethylene oxide by the
SCF MO LCAO CNDO/BW method. Zh Strukt Khim 26(1):133–135
67. Nobes RH, Rodwell WR, Bouma WJ, Radom L (1981) The oxygen analog of the protonated
cyclopropane problem. A theoretical study of the C 2 H 5 O
+
potential energy surface. J Am
Chem Soc 103(8):1913–1922
68. Bock CW, George P, Glusker JP (1993) Ab initio molecular orbital studies on C 2 H 5 O
+
and
C 2 H 4 FO
+
: oxonium ion, carbocation, protonated aldehyde, and related transition-state structures. J Org Chem 58(21):5816–5825
69. Zhao Y, Truhlar DG (2007) How well can new-generation density functionals describe protonated epoxides where older functionals fail? J Org Chem 72(1):295–298
70. Carlier PR, Deora N, Crawford TD (2006) Protonated 2-methyl-1,2-epoxypropane: a challenging problem for density functional theory. J Org Chem 71(4):1592–1597
71. Frenking G, Kato H, Fukui K (1975) An MO-theoretical treatment of the cationic ring-opening polymerisation. I. Ethylene oxide. Bull Chem Soc 45(1):6–12
72. F de Sousa (2010) Theoretical study of acid-catalyzed hydrolysis of epoxides. J Phys Chem
A 114(15):5187–6194
73. Ford GP, Smith CT (1987) Gas-phase hydrolysis of protonated oxirane. Ab initio and
semiempirical molecular orbital calculations. J Am Chem Soc 109(5):1325–1331
74. Coxon JM, Maclagan DGAR, Rauk A, Thorpe AJ, Whalen D (1997) Rearrangement of protonated propene oxide to protonated propanal. J Am Chem Soc 119(20):4712–4718
75. Korzan R, Upton B, Turnbull K, Seybold PG (2010) Quantum chemical study of the energetics and directionality of acid-catalyzed aromatic epoxide ring openings. Int J Quant Chem
110(15):2931–2937
322
51. Omoto K, Fujumoto H (2000) Theoretical study of activation of oxirane by bidentate acids. J
Org Chem 65(8):2464–2471
52. Shibaev AYu, Astrat’eva NV, Tereshchenko GF (1984) Quantum-chemical study of ethylene
oxide amination. Zh Obsh Khim 54(12):2744–2747
53. Lundin A, Panas I, Ahlberg E (2009) Quantum chemical modeling of propene and butene
epoxidation with hydrogen peroxide. J Phys Chem A 113(1):282–290
54. Zheng Y, Zhang J (2010) Interface water catalysis of the epoxide opening. Chem Phys Chem
11(1):65–69
55. Long FA, Pritchard JG (1956) Hydrolysis of substituted ethylene oxides in H 2 O
18
solutions.
J Am Chem Soc 78(12):2663–2667
56. Parker RE, Isaacs MS (1956) Mechanisms of epoxide reactions. Chem Rev 59(4):737–799
57. Pritchard JG, Long FA (1956) Kinetics and mechanism of the acid-catalyzed hydrolysis of
substituted ethylene oxides. J Am Chem Soc 78(12):2667
58. Taft RW (1952) The Dependence of the rate of hydration of isobutene on the acidity function,
H 0 , and the mechanism for olefin hydration in aqueous acids. J Am Chem Soc 74(21):5372–
5376
59. Wohl RA (1974) The Mechanism of the acid-catalized king opening of epoxides. A reinterpretative review. Chimia 28(1):1–5
60. Okovytyy S, Gorb L, Leszczynski J (2001) New insight on the mechanism of 2-oxabicyclobutane fragmentation. A high-level ab initio study. Tetrahedron 57(8):1509–15013
61. Lebedev NN, Guskov KA (1963) Reaction of α-oxides. II. Kinetics of the reactions of ethylene oxides with acetic and monochloroacetic acids. Kinet Katal 4(1):116–127
62. Lebedev NN, Kozlov VM (1966) Kinetics and mechanism of reaction of ethylene oxide and
acids. Zh Obsh Khim 2(2):261–265
63. Kakiuchi H, Tijima T (1980) The ring-opening reactions of propylene oxide with chloroacetic acids. Tetrahedron 36(8):1011–1016
64. Stepanov EG, Podgornova VA, Ustavshchikov BF (1976) Effect of the structure of the carboxylic acid on the reactivity in the reaction with propylene oxide. Osnovn Organ Sintez i
Neftekhimiya 6:29–31
65. Kretova EN, Podgornova VA, Bastrakova ZA, Chagina NT (1984) Zh Fizich Khim
58(11):2885–2887
66. Kretova EN (1985) Calculation of the electronic structure of protonated ethylene oxide by the
SCF MO LCAO CNDO/BW method. Zh Strukt Khim 26(1):133–135
67. Nobes RH, Rodwell WR, Bouma WJ, Radom L (1981) The oxygen analog of the protonated
cyclopropane problem. A theoretical study of the C 2 H 5 O
+
potential energy surface. J Am
Chem Soc 103(8):1913–1922
68. Bock CW, George P, Glusker JP (1993) Ab initio molecular orbital studies on C 2 H 5 O
+
and
C 2 H 4 FO
+
: oxonium ion, carbocation, protonated aldehyde, and related transition-state structures. J Org Chem 58(21):5816–5825
69. Zhao Y, Truhlar DG (2007) How well can new-generation density functionals describe protonated epoxides where older functionals fail? J Org Chem 72(1):295–298
70. Carlier PR, Deora N, Crawford TD (2006) Protonated 2-methyl-1,2-epoxypropane: a challenging problem for density functional theory. J Org Chem 71(4):1592–1597
71. Frenking G, Kato H, Fukui K (1975) An MO-theoretical treatment of the cationic ring-opening polymerisation. I. Ethylene oxide. Bull Chem Soc 45(1):6–12
72. F de Sousa (2010) Theoretical study of acid-catalyzed hydrolysis of epoxides. J Phys Chem
A 114(15):5187–6194
73. Ford GP, Smith CT (1987) Gas-phase hydrolysis of protonated oxirane. Ab initio and
semiempirical molecular orbital calculations. J Am Chem Soc 109(5):1325–1331
74. Coxon JM, Maclagan DGAR, Rauk A, Thorpe AJ, Whalen D (1997) Rearrangement of protonated propene oxide to protonated propanal. J Am Chem Soc 119(20):4712–4718
75. Korzan R, Upton B, Turnbull K, Seybold PG (2010) Quantum chemical study of the energetics and directionality of acid-catalyzed aromatic epoxide ring openings. Int J Quant Chem
110(15):2931–2937