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1
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Eastham S.A., Ingham S.P., Hallett M.R., Herbert J., Quayle P., and Raftery J. Tetrahedron Lett. 47 (2006) 2299-2304
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(2006)
Tetrahedron Lett.
, vol.47
, pp. 2299-2304
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Eastham, S.A.1
Ingham, S.P.2
Hallett, M.R.3
Herbert, J.4
Quayle, P.5
Raftery, J.6
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5
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0033998175
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For mechanistic studies, see:
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For mechanistic studies, see:. Barluenga J., Aznar F., Gutiérrez I., Martín A., Garcia-Granda S., and Llorca-Baragaño M.A. J. Am. Chem. Soc. 122 (2000) 1314-1324
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(2000)
J. Am. Chem. Soc.
, vol.122
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Barluenga, J.1
Aznar, F.2
Gutiérrez, I.3
Martín, A.4
Garcia-Granda, S.5
Llorca-Baragaño, M.A.6
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14
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0025040240
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For the regiochemical outcome from alkoxyacetylenes in Dötz reactions, see
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For the regiochemical outcome from alkoxyacetylenes in Dötz reactions, see. King J., Quayle P., and Malone J.F. Tetrahedron Lett. 31 (1990) 5221-5224
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(1990)
Tetrahedron Lett.
, vol.31
, pp. 5221-5224
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King, J.1
Quayle, P.2
Malone, J.F.3
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20
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0001032829
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For an extensive study, see This study also details the reactions of dihydropyranylchromium carbene complexes which prefer to undergo benzannulation rather than cyclopentannulation reactions with simple alkynes.
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For an extensive study, see. Wulff W.D., Bax B.M., Brandwold T.A., Chan K.S., Gilbert A.M., Hsung R.P., Mitchell J., and Clardy J. Organometallics 13 (1994) 102-126 This study also details the reactions of dihydropyranylchromium carbene complexes which prefer to undergo benzannulation rather than cyclopentannulation reactions with simple alkynes.
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(1994)
Organometallics
, vol.13
, pp. 102-126
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Wulff, W.D.1
Bax, B.M.2
Brandwold, T.A.3
Chan, K.S.4
Gilbert, A.M.5
Hsung, R.P.6
Mitchell, J.7
Clardy, J.8
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21
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9944247495
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The synthesis of cyclopentenones via alternate transition metal reactions are however legion, see: and references therein
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The synthesis of cyclopentenones via alternate transition metal reactions are however legion, see:. Gibson S.E., Lewis S.E., and Mainolfi N. J. Organomet. Chem. 689 (2004) 3873-3890 and references therein
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(2004)
J. Organomet. Chem.
, vol.689
, pp. 3873-3890
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Gibson, S.E.1
Lewis, S.E.2
Mainolfi, N.3
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22
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33746858239
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note
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Regiochemistry by anology.
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23
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33746831353
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note
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The remainder of the mass balance proved to be an intractable mixture, however only one regiosisomer of the benzannulated product was observed.
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24
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0001089271
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Bos M.E., Wulff W.D., Miller R.A., Chamberlin S., and Brandvold T.A. J. Am. Chem. Soc. 113 (1991) 9293-9319
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(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 9293-9319
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Bos, M.E.1
Wulff, W.D.2
Miller, R.A.3
Chamberlin, S.4
Brandvold, T.A.5
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25
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33746811149
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note
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The use of less polar solvents in such reactions usually results in an increase in benzannulation at the expense of cyclopentannulation as detailed in Ref. 4.
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26
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0012145090
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For related silicon migrations in Dötz reactions see: Ref. 1 and
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For related silicon migrations in Dötz reactions see: Ref. 1 and. Moser W.H., Sun L., and Huffman J.C. Org. Lett. 3 (2001) 3389-3391
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(2001)
Org. Lett.
, vol.3
, pp. 3389-3391
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Moser, W.H.1
Sun, L.2
Huffman, J.C.3
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27
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0034826928
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Fogel L., Hsung R.P., Wulff W.D., Sommer R.D., and Rheingold A.L. J. Am. Chem. Soc. 12 (2001) 5580-5581
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(2001)
J. Am. Chem. Soc.
, vol.12
, pp. 5580-5581
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Fogel, L.1
Hsung, R.P.2
Wulff, W.D.3
Sommer, R.D.4
Rheingold, A.L.5
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33746838267
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To our knowledge there is only one other mention of a completion reaction in an intermolecular Dötz reaction, see:. Liebskind L.S. (Ed), JAI Press, London
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To our knowledge there is only one other mention of a completion reaction in an intermolecular Dötz reaction, see:. Wulff W.D. In: Liebskind L.S. (Ed). Advances in Metal-Organic Chemistry Vol. 1 (1988), JAI Press, London 356-357
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(1988)
Advances in Metal-Organic Chemistry
, vol.1
, pp. 356-357
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Wulff, W.D.1
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32
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0000506698
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In this case the regiochemistry of alkyne incorporation was inferred by analogy and not proven. For intramolecular capture of unsymmetrical diynes, see
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In this case the regiochemistry of alkyne incorporation was inferred by analogy and not proven. For intramolecular capture of unsymmetrical diynes, see. Wulff W.D., Kaesler R.W., Peterson G.A., and Tang P.-C. J. Am. Chem. Soc. 107 (1985) 1060-1062
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(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 1060-1062
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Wulff, W.D.1
Kaesler, R.W.2
Peterson, G.A.3
Tang, P.-C.4
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33
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84865666635
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For a discussion of the kinetics, see:
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For a discussion of the kinetics, see:. Fischer H., Mühlemer J., Märkl R., and Dötz K.H. Chem. Ber. 115 (1982) 1355-1362
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(1982)
Chem. Ber.
, vol.115
, pp. 1355-1362
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Fischer, H.1
Mühlemer, J.2
Märkl, R.3
Dötz, K.H.4
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34
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84985559908
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For an early overview of the mechanism of this reaction, see:
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For an early overview of the mechanism of this reaction, see:. Fischer H., and Dötz K.H. Angew. Chem., Int. Ed. Engl. 23 (1984) 587-608
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(1984)
Angew. Chem., Int. Ed. Engl.
, vol.23
, pp. 587-608
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Fischer, H.1
Dötz, K.H.2
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35
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0141905306
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For a review of the physical organic chemistry of this system, see:
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For a review of the physical organic chemistry of this system, see:. Bernasconi C.F. Adv. Phys. Org. Chem. 37 (2002) 137-237
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(2002)
Adv. Phys. Org. Chem.
, vol.37
, pp. 137-237
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Bernasconi, C.F.1
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37
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33746851333
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note
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13C NMR data:{A figure is presented} (cpd. i: Gulías, M.; Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2003, 5, 1975-1977; cpd. ii: Buckley, D. J.; McKervey, M. A. J. Chem. Soc., Perkin Trans. 1 1985, 2193-2200).
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17c,17b a similar regiochemical divergence between benzannulation and cyclopentannulation.
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39
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33746860885
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We were also unable to isolate any of the alternate cyclopentenone iii from this particular reaction.{A figure is presented}.
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41
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33748226733
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The formation of alkyne-chromium carbene chelate complexes has been documented
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The formation of alkyne-chromium carbene chelate complexes has been documented. Dötz K.H., Schäfer T., Kroll F., and Harms K. Angew. Chem., Int. Ed., Engl. 31 (1992) 1236-1238
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(1992)
Angew. Chem., Int. Ed., Engl.
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, pp. 1236-1238
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Dötz, K.H.1
Schäfer, T.2
Kroll, F.3
Harms, K.4
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33845550670
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Interestingly π-complex iv is unstable and rearranges at temperatures above -30 °C to indene v:{A figure is presented}.
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Foley H.C., Strubinger L.M., Targos T.S., and Geoffroy G.L. J. Am. Chem. Soc. 105 (1983) 3064-3073 Interestingly π-complex iv is unstable and rearranges at temperatures above -30 °C to indene v:{A figure is presented}.
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(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 3064-3073
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Foley, H.C.1
Strubinger, L.M.2
Targos, T.S.3
Geoffroy, G.L.4
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46
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0348185308
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Eastham S.A., Herbert J., Painter J.E., Patel P., and Quayle P. Synlett (1998) 61-63
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(1998)
Synlett
, pp. 61-63
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Eastham, S.A.1
Herbert, J.2
Painter, J.E.3
Patel, P.4
Quayle, P.5
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For leading references see
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For leading references see. Barluenga J., Alonso J., Rodríguez F., and Fañanás F.J. Angew. Chem., Int. Ed. 39 (2000) 2460-2462
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(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 2460-2462
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Barluenga, J.1
Alonso, J.2
Rodríguez, F.3
Fañanás, F.J.4
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53
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0037442901
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Barluenga J., Ballesteros A., de la Rúa R.R., Santamaria J., Rubio E., and Tomás M. J. Am. Chem. Soc. 125 (2003) 1834-1842
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(2003)
J. Am. Chem. Soc.
, vol.125
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Barluenga, J.1
Ballesteros, A.2
de la Rúa, R.R.3
Santamaria, J.4
Rubio, E.5
Tomás, M.6
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56
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0035831103
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For the effects of additives in such reactions, see and references cited therein
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For the effects of additives in such reactions, see. Flynn B.L., Schirmer H., Duetsch M., and de Meijere A. J. Org. Chem. 66 (2001) 1747-1754 and references cited therein
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(2001)
J. Org. Chem.
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Flynn, B.L.1
Schirmer, H.2
Duetsch, M.3
de Meijere, A.4
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