메뉴 건너뛰기




Volumn , Issue , 2007, Pages 41-96

The Effect of Pressure on Organic Reactions: Basic Principles and Mechanistic Applications

Author keywords

Cycloadditions; Diels alder reactions; Effect of pressure; Organic reactions; Pericydic rearrangements

Indexed keywords

CYCLOADDITION;

EID: 84956779029     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527612628.ch02     Document Type: Chapter
Times cited : (7)

References (199)
  • 39
    • 84982076770 scopus 로고
    • W. R. ROTH, S. B. P., Chem. Ber. 1981, 114, 3741.
    • (1981) Chem. Ber. , vol.114 , pp. 3741
    • Roth, W.R.1
  • 40
    • 84956709527 scopus 로고
    • Phd Thesis, Ruhr-Universitat Bochum
    • M. BARTMANN, PhD Thesis, Ruhr-Universitat Bochum, 1980.
    • (1980)
    • Bartmann, M.1
  • 43
    • 84956791295 scopus 로고
    • Diploma Thesis, Ruhr-Universitat Bochum, 1987
    • Phd Thesis, Ruhr-Universitat Bochum
    • V. RUSTER, Diploma Thesis, Ruhr-Universitat Bochum, 1987; PhD Thesis, Ruhr-Universitat Bochum, 1991.
    • (1991)
    • Ruster, V.1
  • 47
    • 84956724958 scopus 로고
    • Ruhr-Universitat Bochum
    • B. M. J. DOGAN, PhD Thesis, Ruhr-Universitat Bochum, 1984.
    • (1984) Phd Thesis
    • Dogan, B.M.J.1
  • 52
    • 84956724672 scopus 로고    scopus 로고
    • The Surprisingly Small Activation Volume Found For The Formation Of The Very Minor [4 + 4] Cyclodimer 16 In The 1,3-Butadiene Dimerization Seems To Be Inconsistent With A Stepwise Mechanism. The Small Ratio 0 = Av5≠ /Av = 0.54 Which Is Substantially Smaller Than That Of The Formation Of 14, 0 = 0.79, And Almost Equal To That Of The Formation Of 15, 0 = 0.59, May Indicate That 13 Is Formed Via A Stepwise [4 + 4] Cycloadditionpassing Through A (Z,Z)-Configured Diradical Intermediate.
    • The surprisingly small activation volume found for the formation of the very minor [4 + 4] cyclodimer 16 in the 1,3-butadiene dimerization seems to be inconsistent with a stepwise mechanism. The small ratio 0 = AV5≠/AV = 0.54 which is substantially smaller than that of the formation of 14, 0 = 0.79, and almost equal to that of the formation of 15, 0 = 0.59, may indicate that 13 is formed via a stepwise [4 + 4] cycloadditionpassing through a (Z,Z)-configured diradical intermediate.
  • 56
    • 0342340883 scopus 로고
    • Serena Software
    • PCMODEL, Serena Software, 1992.
    • (1992)
  • 57
    • 0342876746 scopus 로고
    • In W. F. Le Noble (Ed.), Elsevier, Amsterdam,
    • O. EXNER, in Organic High Pressure Chemistry, W. f. LE NOBLE (Ed.), Elsevier, Amsterdam, 1988, 19-49.
    • (1988) Organic High Pressure Chemistry, , pp. 19-49
    • Exner, O.1
  • 97
    • 0004101860 scopus 로고
    • 2,3-Dipolar Cycloaddition Chemistry,
    • (Ed.), Wiley Interscience, New York,
    • A. PADWA (Ed.), 2,3-Dipolar Cycloaddition Chemistry, Wiley Interscience, New York, 1984.
    • (1984)
    • Padwa, A.1
  • 105
    • 0004231256 scopus 로고
    • In Volume Ii, A. P. Marchand, R. E. Lehr (Eds), Academic Press, New York,
    • L. GHOZEZ, M. J. O'DONNEL, in Pericyclic Reactions, Volume II, A. P. MARCHAND, R. E. LEHR (Eds), Academic Press, New York, 1977.
    • (1977) Pericyclic Reactions,
    • Ghozez, L.1    O'donnel, M.J.2
  • 112
    • 84956844393 scopus 로고    scopus 로고
    • Phd Thesis, Universitat Essen,
    • B. KRAWCZYK, PhD Thesis, Universitat Essen, 1996.
    • (1996)
    • Krawczyk, B.1
  • 121
    • 84956754001 scopus 로고    scopus 로고
    • The Partial Molar Volumes Of Tropone, 1,3-Butadiene And The [6 + 4] Cycloadduct Were Measured By Dogan [35] To Be V = 88.8, 83.1 And 153.2 Cm3 Mol-1, Respectively, At 21 °C And Extrapolated To Be 99.8, 87.9, 154.1 Cm' Mol-1, Respectively, At 60 °C Using The Values Give By Takeshita Et Al. [92] For The Reaction Of Tropone With 2,3-Dimethylbutadiene.
    • The partial molar volumes of tropone, 1,3-butadiene and the [6 + 4] cycloadduct were measured by Dogan [35] to be V = 88.8, 83.1 and 153.2 cm3 mol-1, respectively, at 21 °C and extrapolated to be 99.8, 87.9, 154.1 cm' mol-1, respectively, at 60 °C using the values give by Takeshita et al. [92] for the reaction of tropone with 2,3-dimethylbutadiene.
  • 128
    • 0024827392 scopus 로고
    • Tetrahedron 1989, 45, 7083-7092.
    • N. S. ISAACS, G. N. EL-DIN, Synthesis 1989, 967; Tetrahedron 1989, 45, 7083-7092.
    • (1989) Synthesis , pp. 967
    • Isaacs, N.S.1    El-Din, G.N.2
  • 140
    • 0001694036 scopus 로고
    • The Temperature-Dependent Kinetic Analysis Was Carried Out For This Rearrangement In The Gas Phase Between 142 And 173 °C Leading To The Arrhenius Equation Log K - (11.1 ± 0.3) - (29.3 ± 0.5) Kcal Mol-1'/Rt. In The Gas Phase The Resulting Activation Enthalpy And Entropy, Ah≠= 28.5 Kcal Mol-1 And As≠ = -10.6 Cal Mol-1 K"1, Are Larger Than Those In Benzene Solution (80 °C: Ah≠ = 25.4 Kcal Mol"1 And As≠ = -15.9 Cal Mol-1 K"1: J. Burrows, B. K. Carpenter,
    • The temperature-dependent kinetic analysis was carried out for this rearrangement in the gas phase between 142 and 173 °C leading to the Arrhenius equation log k - (11.1 ± 0.3) - (29.3 ± 0.5) kcal mol-1'/RT. In the gas phase the resulting activation enthalpy and entropy, AH≠= 28.5 kcal mol-1 and AS≠ = -10.6 cal mol-1 K"1, are larger than those in benzene solution (80 °C: AH≠ = 25.4 kcal mol"1 and AS≠= -15.9 cal mol-1 K"1: J. BURROWS, B. K. CARPENTER, J. Am. Chem. Soc. 1981, 103, 6983).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6983
  • 143
    • 84956715976 scopus 로고    scopus 로고
    • Phd Thesis, Universitatessen,
    • J.-S. GEHRKE, PhD Thesis, UniversitatEssen, 1999.
    • (1999)
    • Gehrke, J.-S.1
  • 164
    • 84956761661 scopus 로고    scopus 로고
    • Although The New C-C Bond Is Only Partially Formed In The Transition Structure, The C-H-C Distances Are Obviously Both Within The Range Of Van Der Waals Distances, Whereasin The Product The Non-Bonding (=H2C--H-Ch3-) Distance Is, according to the most stable geometry, larger than the van der Waals distance.
    • Although the new C-C bond is only partially formed in the transition structure, the C-H-C distances are obviously both within the range of van der Waals distances, whereasin the product the non-bonding (=H2C--H-CH3-) distance is,according To The Most Stable Geometry, Larger Than The Van Der Waals Distance.
  • 178
    • 84956830880 scopus 로고    scopus 로고
    • Phd Thesis, Universitat Essen (In Preparation).
    • G. DIERKES, PhD Thesis, Universitat Essen (in preparation).
    • Dierkes, G.1
  • 184
    • 84956823976 scopus 로고    scopus 로고
    • Phd Thesis, Universitat Essen (In Preparation).
    • F. WURCHE, PhD Thesis, Universitat Essen (in preparation).
    • Wurche, F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.