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0001209154
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It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
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13
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0001918119
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It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
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14
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0001209154
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It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
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Buchwald, S.L.1
LaMaire, S.J.2
Nielsen, R.B.3
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King, S.M.5
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15
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0001918119
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It has been reported that the reactivity of alky- or alkenylziconocene chloride derived from the hydrozirconation of alkene or alkyne by Schwartz reagent would be altered by the preparative method of the employed Schwartz reagent. That is, contamination of the Schwartz reagent would have a serious effect on the subsequent reactivity of the derived zirconocene complexes. See Ref. 17a. To avoid the uncertainty, the Schwartz reagent prepared by the Buchwald's procedure was employed throughout the present reactions. (a) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Tetrahedron Lett. 28:1987;3895 (b) Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.
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16
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0011957994
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For a preliminary report on some aspects of the present study, see Ref. 3f
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For a preliminary report on some aspects of the present study, see Ref. 3f.
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2-C zirconacycles with propargyl halides has been demonstrated. (a) Takahashi T., Tsai F.-Y., Li Y., Wang H., Kondo Y., yamanaka M., Nakajima K., Kotora M. J. Am. Chem. Soc. 124:2002;5059 (b) Kotora M., Noguchi Y., Takahashi T. Collect. Czech. Chem. Commun. 64:1999;1119.
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2-C zirconacycles with propargyl halides has been demonstrated. (a)
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2-C zirconacycles with propargyl halides has been demonstrated. (a) Takahashi T., Tsai F.-Y., Li Y., Wang H., Kondo Y., yamanaka M., Nakajima K., Kotora M. J. Am. Chem. Soc. 124:2002;5059 (b) Kotora M., Noguchi Y., Takahashi T. Collect. Czech. Chem. Commun. 64:1999;1119.
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0011958723
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note
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One of the reviewers pointed out the mechanistic aspects for the present Cu(I)-catalyzed coupling reactions with allylic halides: (1) an intervention of the oxyCu carbene as an actual reactive species, and (2) stereochemical aspects of the products. The reviewer suggested the possibility for the formation of cyclopropyl alkoxide by the addition of the oxyCu carbene species to the double bond of allylic halides and subsequent elimination of the halogen giving products 2. We assume that the present cross-coupling reactions would proceed through the nucleophilic attack of acyl-Cu 9 to the allylic halide, because of the recovery of starting materials in the reactions of homoallylic halide derivatives. However, we must await further studies to describe a detailed mechanism for the reaction. We appreciate the reviewer for generous suggestions, and the reaction mechanism will be reported in due course.
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26
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0003417469
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B.M. Trost, & I. Fleming. Oxford: Pergamon. p 169 and the references cited therein
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Kozlowski J.A. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 1991;Pergamon, Oxford. p 169 and the references cited therein.
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