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1
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0001737656
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Turro, N. J.; Butcher, J. A.; Moss, R. A.; Guo, W.; Munjal, R. C.; Fedorynski, M. J. Am. Chem. Soc. 1980, 102, 7576.
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(1980)
J. Am. Chem. Soc
, vol.102
, pp. 7576
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Turro, N.J.1
Butcher, J.A.2
Moss, R.A.3
Guo, W.4
Munjal, R.C.5
Fedorynski, M.6
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2
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0003673645
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Review:, Platz, M. S, Ed, Plenum Press: New York
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Review: Moss, R. A.; Turro, N. J. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; pp 213 f.
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(1990)
Kinetics and Spectroscopy of Carbenes and Biradicals
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Moss, R.A.1
Turro, N.J.2
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3
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33845278072
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Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595.
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(1988)
J. Am. Chem. Soc
, vol.110
, pp. 5595
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Jackson, J.E.1
Soundararajan, N.2
Platz, M.S.3
Liu, M.T.H.4
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4
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0002312550
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Brinker, U. H, Ed, JAI Press: Greenwich, CT
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(a) Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 1, pp 89 f.
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(1994)
In Advances in Carbene Chemistry
, vol.1
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Jackson, J.E.1
Platz, M.S.2
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5
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0141472371
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Brinker, U. H, Ed, Elsevier: Amsterdam
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(b) Merrer, D. C.; Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Elsevier: Amsterdam, 2001; Vol. 3, pp 53 f.
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(2001)
In Advances in Carbene Chemistry
, vol.3
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Merrer, D.C.1
Moss, R.A.2
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6
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34250685756
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Preliminary results were presented at the 18th IUPAC International Conference on Reactive Intermediates, Warsaw, Poland, August 23, 2006, and are contained in a written version of that talk: Moss, R. A.; Tian, J.; Chu, G.; Sauers, R. R.; Krogh-Jespersen, K. Pure Appl. Chem. 2007, 79, 993. Neither the spectra themselves, nor descriptions of the time-dependent dynamics of the carbene-solvent and carbene-diazirine reactions, are contained in this report.
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Preliminary results were presented at the 18th IUPAC International Conference on Reactive Intermediates, Warsaw, Poland, August 23, 2006, and are contained in a written version of that talk: Moss, R. A.; Tian, J.; Chu, G.; Sauers, R. R.; Krogh-Jespersen, K. Pure Appl. Chem. 2007, 79, 993. Neither the spectra themselves, nor descriptions of the time-dependent dynamics of the carbene-solvent and carbene-diazirine reactions, are contained in this report.
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8
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34547866249
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1H NMR vs an internal dioxane standard.
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1H NMR vs an internal dioxane standard.
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9
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34547865490
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Details of our LFP apparatus appear in the Supporting Information
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Details of our LFP apparatus appear in the Supporting Information.
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10
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34547863997
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See the Supporting Information for references to and details of the calculations
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See the Supporting Information for references to and details of the calculations.
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11
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0000228319
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7481; cf, p
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Pliego, J. R., Jr.; De Almeida, W. B.; Celebi, C., Zhu, Z.; Platz, M. S. J. Phys. Chem. A 1999, 103, 7481; cf., p 7484.
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(1999)
J. Phys. Chem. A
, vol.103
, pp. 7484
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Pliego Jr., J.R.1
De Almeida, W.B.2
Celebi, C.3
Zhu, Z.4
Platz, M.S.5
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12
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0000647718
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(a) Bonneau, R.; Liu, M. T. H.; Rayez, M. T. J. Am. Chem. Soc. 1989, 111, 5973.
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(1989)
J. Am. Chem. Soc
, vol.111
, pp. 5973
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Bonneau, R.1
Liu, M.T.H.2
Rayez, M.T.3
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13
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0000057159
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(b) Dix, E. J.; Herman, M. S.; Goodman, J. L. J. Am. Chem. Soc. 1993, 125, 10424.
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(1993)
J. Am. Chem. Soc
, vol.125
, pp. 10424
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Dix, E.J.1
Herman, M.S.2
Goodman, J.L.3
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16
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34547870286
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The decay of ylide 5a should provide an azine [MeClC=N-N=CClMe, This product (in addition to vinyl chloride) was detected by GC-MS after 350 nm photolysis of diazirine 4a in pentane. We have not kinetically monitored the decay of ylide 5a
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The decay of ylide 5a should provide an azine [MeClC=N-N=CClMe]. This product (in addition to vinyl chloride) was detected by GC-MS after 350 nm photolysis of diazirine 4a in pentane. We have not kinetically monitored the decay of ylide 5a.
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17
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0035249423
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Celebi, S.; Tsao, M.-L.; Platz, M. S. J. Phys. Chem. A 2001, 105, 1158.
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(2001)
J. Phys. Chem. A
, vol.105
, pp. 1158
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Celebi, S.1
Tsao, M.-L.2
Platz, M.S.3
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18
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0346993321
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Preslowski, S. I.; Zorba, A.; Thamattoor, D. M.; Tippmann, E. M.; Platz, M. S. Tetrahedron Lett. 2004, 45, 485.
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(2004)
Tetrahedron Lett
, vol.45
, pp. 485
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Preslowski, S.I.1
Zorba, A.2
Thamattoor, D.M.3
Tippmann, E.M.4
Platz, M.S.5
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19
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0035922559
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(a) Tsao, M.-L.; Zhu, Z.; Platz, M. S. J. Phys. Chem. A 2001, 105, 8413.
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(2001)
J. Phys. Chem. A
, vol.105
, pp. 8413
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Tsao, M.-L.1
Zhu, Z.2
Platz, M.S.3
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20
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0141740714
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(b) Sun, Y.; Tippmann, E. M.; Platz, M. S. Org. Lett. 2003, 5, 1305.
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(2003)
Org. Lett
, vol.5
, pp. 1305
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Sun, Y.1
Tippmann, E.M.2
Platz, M.S.3
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21
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2442473013
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(c) Tippmann, E. M.; Platz, M. S.; Svir, I. B.; Klymenko, O. V. J. Am. Chem. Soc. 2004, 126, 5750.
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(2004)
J. Am. Chem. Soc
, vol.126
, pp. 5750
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Tippmann, E.M.1
Platz, M.S.2
Svir, I.B.3
Klymenko, O.V.4
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22
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0033532866
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Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269.
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(1999)
J. Am. Chem. Soc
, vol.121
, pp. 6269
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Krogh-Jespersen, K.1
Yan, S.2
Moss, R.A.3
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23
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34547918087
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The LFP-UV spectrum of MeCCl in anisole is identical under air or nitrogen, excluding the intervention of a carbene-oxygen ylide carbonyl oxide
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The LFP-UV spectrum of MeCCl in anisole is identical under air or nitrogen, excluding the intervention of a carbene-oxygen ylide (carbonyl oxide).
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24
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34547883630
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We would expect the MP2 method to produce the more accurate interaction energies because dispersion interactions are included in this method. However, MP2 calculations scale poorly with molecular size and are cumbersome to use in exhaustive studies of potential energy surfaces for larger molecular systems. DFT, on the other hand, scales favorably with system size but does not generally include dispersion interactions in the functionals employed. That the PBEPBE functionals tend to err on the side of overbinding, whereas the B3LYP functionals underbind, particularly for weak interactions, probably works in our favor here.
-
We would expect the MP2 method to produce the more accurate interaction energies because dispersion interactions are included in this method. However, MP2 calculations scale poorly with molecular size and are cumbersome to use in exhaustive studies of potential energy surfaces for larger molecular systems. DFT, on the other hand, scales favorably with system size but does not generally include dispersion interactions in the functionals employed. That the PBEPBE functionals tend to err on the side of overbinding, whereas the B3LYP functionals underbind, particularly for weak interactions, probably works in our favor here.
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25
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0003505803
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Wiley: New York
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Nishio, M.; Hirota, M.; Umezawa, Y. The CH-π Interaction: Evidence, Nature, and Consequences; Wiley: New York, 1998.
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(1998)
The CH-π Interaction: Evidence, Nature, and Consequences
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Nishio, M.1
Hirota, M.2
Umezawa, Y.3
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26
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34547896375
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Attempts to reorient the carbene Me group of 6d toward the phenyl center resulted (upon structural reoptimization) in rotation of the carbene back to its original position or in migration to complex 6c.
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Attempts to reorient the carbene Me group of 6d toward the phenyl center resulted (upon structural reoptimization) in rotation of the carbene back to its original position or in migration to complex 6c.
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27
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34547910771
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Consideration of the gas-phase MP2/6-311+G(d) and B3LYP/6-311+G(d) energies (Supporting Information) does not alter this conclusion.
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Consideration of the gas-phase MP2/6-311+G(d) and B3LYP/6-311+G(d) energies (Supporting Information) does not alter this conclusion.
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28
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34547911167
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MP2 and B3LYP results (Supporting Information) indicate that the THF and dioxane ylides could be less favorable than anisole O-ylide 6d; however, the relative destabilization is not large.
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MP2 and B3LYP results (Supporting Information) indicate that the THF and dioxane ylides could be less favorable than anisole O-ylide 6d; however, the relative destabilization is not large.
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29
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34547885553
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The local σ → p MeCCl transition is computed at 574.3 nm (f = 0.04) in 7a and at 498.6 nm (f = 0.04)in 7b.
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The "local" σ → p MeCCl transition is computed at 574.3 nm (f = 0.04) in 7a and at 498.6 nm (f = 0.04)in 7b.
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30
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0000839788
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(a) Sugiyama, M. H.; Celebi, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 966.
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(1992)
J. Am. Chem. Soc
, vol.114
, pp. 966
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Sugiyama, M.H.1
Celebi, S.2
Platz, M.S.3
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31
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0000865948
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(b) Merrer, D. C.; Moss, R. A.; Liu, M. T. H.; Banks, J. T.; Ingold, K. U. J. Org. Chem. 1998, 63, 3010.
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(1998)
J. Org. Chem
, vol.63
, pp. 3010
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Merrer, D.C.1
Moss, R.A.2
Liu, M.T.H.3
Banks, J.T.4
Ingold, K.U.5
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33
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0000241299
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Brinker, U. H, Ed, JAI Press: Stamford, CT
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(b) Platz, M. S. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Stamford, CT, 1998; Vol. 2, pp 133 f.
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(1998)
Advances in Carbene Chemistry
, vol.2
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Platz, M.S.1
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35
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34547894374
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1H NMR vs an internal dioxane standard.
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1H NMR vs an internal dioxane standard.
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36
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0000460838
-
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Jackson, J. E.; Soundararajan, N.; White, W.; Liu, M. T. H.; Bonneau, R.; Platz, M. S. J. Am. Chem. Soc., 1989, 111, 6874.
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(1989)
J. Am. Chem. Soc
, vol.111
, pp. 6874
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Jackson, J.E.1
Soundararajan, N.2
White, W.3
Liu, M.T.H.4
Bonneau, R.5
Platz, M.S.6
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37
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34547879778
-
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H can also be determined by monitoring the decay of 2b at 310 nm (ref 27), but product β-chlorostyrene absorbs in the 290-300 nm region. Following the 576 nm σ → p absorption is simpler.
-
H can also be determined by monitoring the decay of 2b at 310 nm (ref 27), but product β-chlorostyrene absorbs in the 290-300 nm region. Following the 576 nm σ → p absorption is simpler.
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39
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34547878832
-
-
This figure shows a composite of the carbene σ → p absorbance at 50 ns after the laser pulse and the carbene-diazirine ylide at greater elapsed time (1000 ns) so that the intensities of both signals are maximized
-
This figure shows a "composite" of the carbene σ → p absorbance at 50 ns after the laser pulse and the carbene-diazirine ylide at greater elapsed time (1000 ns) so that the intensities of both signals are maximized.
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43
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0032890212
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Yao, G.; Rempala, P.; Bashore, C.; Sheridan, R. S. Tetrahedron Lett. 1999, 40, 17.
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(1999)
Tetrahedron Lett
, vol.40
, pp. 17
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Yao, G.1
Rempala, P.2
Bashore, C.3
Sheridan, R.S.4
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44
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84982056158
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The steric substituent constants of t-butyl and 1-adamantyl are comparable: Hellmann, G.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1979, 112, 1808.
-
The steric substituent constants of t-butyl and 1-adamantyl are comparable: Hellmann, G.; Beckhaus, H.-D.; Rüchardt, C. Chem. Ber. 1979, 112, 1808.
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45
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34547863996
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These spectra were acquired 50 ns after the laser pulse
-
These spectra were acquired 50 ns after the laser pulse.
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46
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0000395861
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Ho, G.-J.; Krogh-Jespersen, K.; Moss, R. A.; Shen, S.; Sheridan, R. S.; Subramanian, R. J. Am. Chem. Soc. 1989, 111, 6875.
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(1989)
J. Am. Chem. Soc
, vol.111
, pp. 6875
-
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Ho, G.-J.1
Krogh-Jespersen, K.2
Moss, R.A.3
Shen, S.4
Sheridan, R.S.5
Subramanian, R.6
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48
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0028807750
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(b) Moss, R. A.; Ma, W.; Merrer, D. C.; Xue, S. Tetrahedron Lett. 1995, 36, 8761.
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(1995)
Tetrahedron Lett
, vol.36
, pp. 8761
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Moss, R.A.1
Ma, W.2
Merrer, D.C.3
Xue, S.4
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49
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34547875147
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2: cf., ref 25b.
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2: cf., ref 25b.
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50
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37049109895
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R = t-Bu: Moss, R. A.; Munjal, R. C. Chem. Commun. 1978, 775.
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(b) R = t-Bu: Moss, R. A.; Munjal, R. C. Chem. Commun. 1978, 775.
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51
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0001716360
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5: Moss, R. A.; Shen, S.; Krogh-Jespersen, K.; Potenza, J. A.; Schugar, H. J.; Munjal, R. C. J. Am. Chem. Soc. 1986, 108, 134.
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5: Moss, R. A.; Shen, S.; Krogh-Jespersen, K.; Potenza, J. A.; Schugar, H. J.; Munjal, R. C. J. Am. Chem. Soc. 1986, 108, 134.
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