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2
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0004269715
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Renaud, P.; Sibi. M., Eds.; Wiley-VCH: Weinheim, Chap 5
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(b) Hartung, J.; Suárez, E.; Rodriguez, M. S.; Boukouvalas, J.; Haynes, R. K. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi. M., Eds.; Wiley-VCH: Weinheim, 2001, Chap 5.
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Radicals in Organic Synthesis
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Hartung, J.1
Suárez, E.2
Rodriguez, M.S.3
Boukouvalas, J.4
Haynes, R.K.5
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4
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20644448549
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note
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To our knowledge, rate data for the addition of alkoxyl radicals to alkynes have not been determined so far.
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14
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20644449428
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PhD Thesis; Universität Kiel: Germany
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. induced self-terminating radical oxygenations was verified by DFT calculations: Dreessen, T. PhD Thesis; Universität Kiel: Germany, 2004.
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(2004)
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Dreessen, T.1
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15
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0001053575
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Examples for the intermolecular addition of O-centered radicals to C=C triple bonds: (a) Walling, C.; Clark, R. T. J. Am. Chem. Soc. 1974, 96, 4530.
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(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 4530
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Walling, C.1
Clark, R.T.2
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17
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37049072977
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(c) Bottle, S.; Busfield, W. K.; Jenkins, I. D.; Skelton, B. W.; White, A. H.; Rizzardo. E.; Solomon, D. H. J. Chem. Soc., Perkin Trans. 2 1991, 1001.
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(1991)
J. Chem. Soc., Perkin Trans. 2
, pp. 1001
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Bottle, S.1
Busfield, W.K.2
Jenkins, I.D.3
Skelton, B.W.4
White, A.H.5
Rizzardo, E.6
Solomon, D.H.7
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18
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20644448167
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note
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4-8
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19
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0001358171
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Kim, S.; Lim, C. J.; Song, S.-E.; Kang, H.-Y. Synlett 2001, 688.
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(2001)
Synlett
, pp. 688
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Kim, S.1
Lim, C.J.2
Song, S.-E.3
Kang, H.-Y.4
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20
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20644445809
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note
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8
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21
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20644434548
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note
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4a
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22
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0141704726
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Gaussian, Inc.: Pittsburgh PA
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, R. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda. R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul. A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng. C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh PA, 2003.
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(2003)
Gaussian 03, Revision B.04
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Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, R.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Adamo, C.36
Jaramillo, J.37
Gomperts, R.38
Stratmann, R.E.39
Yazyev, O.40
Austin, A.J.41
Cammi, R.42
Pomelli, C.43
Ochterski, W.44
Ayala, P.Y.45
Morokuma, K.46
Voth, G.A.47
Salvador, P.48
Dannenberg, J.J.49
Zakrzewski, V.G.50
Dapprich, S.51
Daniels, A.D.52
Strain, M.C.53
Farkas, O.54
Malick, D.K.55
Rabuck, A.D.56
Raghavachari, K.57
Foresman, J.B.58
Ortiz, J.V.59
Cui, Q.60
Baboul, A.G.61
Clifford, S.62
Cioslowski, J.63
Stefanov, B.B.64
Liu, G.65
Liashenko, A.66
Piskorz, P.67
Komaromi, I.68
Martin, R.L.69
Fox, D.J.70
Keith, T.71
Al-Laham, M.A.72
Peng, C.Y.73
Nanayakkara, A.74
Challacombe, M.75
Gill, P.M.W.76
Johnson, B.77
Chen, W.78
Wong, M.W.79
Gonzalez, C.80
Pople, J.A.81
more..
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23
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0036399236
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Actually, the energy barrier for the addition of alkyl radicals to the carbonyl oxygen was calculated to be significantly higher than for the addition to the carbon site of a carbonyl bond: (a) Hippler, H.; Viskolcz, B. Phys. Chem. Chem. Phys. 2002, 4, 4663.
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(2002)
Phys. Chem. Chem. Phys.
, vol.4
, pp. 4663
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Hippler, H.1
Viskolcz, B.2
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24
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1242314249
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(b) Henry, D. J.; Coote, M. L.; Gomez-Balderas, R.; Radom, L. J. Am. Chem. Soc. 2004, 126, 1732.
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(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 1732
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Henry, D.J.1
Coote, M.L.2
Gomez-Balderas, R.3
Radom, L.4
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25
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0037194948
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-
and literature cited therein
-
Henry, D. J.; Parkinson, C. J.; Radom, L. J. Phys. Chem. A 2002, 106, 7927; and literature cited therein.
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(2002)
J. Phys. Chem. A
, vol.106
, pp. 7927
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-
Henry, D.J.1
Parkinson, C.J.2
Radom, L.3
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26
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20644444282
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note
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Steric repulsion by the bulky methyl substituents may be the reason for the slightly longer O-X bond in the terf-butyl substituted radical 12.
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27
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20644432384
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note
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16a
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28
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1842737688
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This is in agreement with literature, where comparison of the reaction barriers for radical reactions with these two functionals has shown the B3LYP barriers to be somewhat too low, whereas the BHandHLYP barriers are slightly too high in many cases; see for example: Wang, Y.; Grimme, S.; Zipse, H. J. Phys. Chem. A 2004, 108, 2324.
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(2004)
J. Phys. Chem. A
, vol.108
, pp. 2324
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-
Wang, Y.1
Grimme, S.2
Zipse, H.3
-
29
-
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20644443865
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-
note
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BHandHLYP calculations performed with the cc-pVDZ, aug-cc-pVDZ and cc-pVTZ basis set, respectively, resulted in comparable results for ΔE‡ and ΔE than obtained with the 6-311G** basis set. MP2 calculations with these basis sets generally reflected the results of the B 3LYP method.
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