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0142205675
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2-catalyzed case, cyclopropanation in DCE resulted in lower yield of 2a (74%) together with the formation of a substantial amount of allenyl acetate (23%).
-
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45
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0142205676
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note
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3. Purification details are shown in the Experimental Section.
-
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46
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0142236581
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note
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The geometry of the alkenic part in the major product cis-2f was assigned to Z by X-ray diffraction analysis (see Supporting Information). Since the NMR data of trans-2f are similar to those of cis-2f with an exception of cyclopropane ring assignment, we assume that the geometry in trans-2f would be also Z.
-
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47
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0142174545
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note
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The reaction of If with styrene in DCE was not complete even after 36 h.
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49
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Oxidative addition of propargylic acetate to a ruthenium complex leading to o-allenylruthenium acetate E followed by transposition of an acetate group from ruthenium to C-2 of the σ-allenyl ligand is another possible route to the vinylcarbenoid. However, experimental results of no formation of crossover products also rule out such a route where the acetoxy group might be liberated in the system.
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51
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33646142047
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Generation of vinylcarbenoids from propargylic halides, acetates, and alcohols using transition metal hydride complexes has already been reported, and the complexes have been widely applied as metathesis catalysts. The mechanisms of these reactions, however, are apparently different from that of the present hydride-free case. (a) Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867.
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0142236580
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1H NMR spectrum of 2r or 2s, might support the configuration of transcyclopropane.
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57
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0009841005
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The cascade reaction of carbenoid transfer cyclopropanation and [3, 3]sigmatropy has been developed by using a combination of diazoalkanes and rhodium- and copper-catalysts. For leading references of transition metal-catalyzed reactions, see: (a) Davies, H. M. L. Advance in Cycloaddit. 1999, 5, 119.
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64
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0142174544
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The syn stereochemistry of 2t was more clearly determined by NOE analysis. Thus, percentage increments (6% and 5%) in the area intensities of vinyl protons on a cyclopentene ring were observed by irradiation at the two methyl groups of an isopropylidene of 2t, respectively.
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