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This transformation is somewhat reminiscent of the synthesis of phenols by intramolecular Diels-Alder reaction of alkynes with furans in the presence of a base, a reaction that actually takes place by previous isomerization of the alkyne to the allene: (a) Wu, H.-J.; Shao, W.-D. Ying, F.-H. Tetrahedron Lett. 1994, 35, 729-732. (b) Wu, H.-J.; Ying, F.-H.; Shao, W.-D. J. Org. Chem. 1995, 60, 6168-6172.
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The preparation of substrates of Chart 1 is detailed in the Supporting Information.
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0038081443
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note
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Atomic coordinates for the structures of Figures 1 and 2 are given in the Supporting Information.
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61
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84981766367
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For reviews on arene oxides and their isomeric oxepins: (a) Vogel, E.; Günther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 25, 289-296. (c) For a recent lead reference on the structure of arene oxides, see: Jia, Z. S.; Brandt, P.; Thibblin, A. J. Am. Chem. Soc. 2001, 42, 10 147-10 152.
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For reviews on arene oxides and their isomeric oxepins: (a) Vogel, E.; Günther, H. Angew. Chem., Int. Ed. Engl. 1967, 6, 385-401. (b) Boyd, D. R.; Sharma, N. D. Chem. Soc. Rev. 1996, 25, 289-296. (c) For a recent lead reference on the structure of arene oxides, see: Jia, Z. S.; Brandt, P.; Thibblin, A. J. Am. Chem. Soc. 2001, 42, 10 147-10 152.
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0038758093
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note
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f (PM3 calculations) favoring the intermediate that leads to major isomer 42.
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67
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0037743957
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note
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-1 starting from the E isomer of 72; PM3 calculations].
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68
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0034686737
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Calculations on the formation of epoxides by [2+2] cycloaddition/reductive elimination are given as part of the Supporting Information.
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