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Crystallographic data reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no
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Crystallographic data reported in this manuscript have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-726048.
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In a formal sense, the formation of allylic carbocation intermediate by protonation of the center carbon overwhelms that of vinyl cation. However, kinetically favored protonation furnishes the vinyl cation intermediate. This result could be explained by stereoelectronic factors. Because the allene structure is nonplanar, an initial protonation of the center carbon leads to a twisted structure that avoids allylic conjugation. See: a K. B. Wiberg, C. M. Breneman, T. J. LePage, J. Am. Chem. Soc. 1990, 112, 61
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In a formal sense, the formation of allylic carbocation intermediate by protonation of the center carbon overwhelms that of vinyl cation. However, kinetically favored protonation furnishes the vinyl cation intermediate. This result could be explained by stereoelectronic factors. Because the allene structure is nonplanar, an initial protonation of the center carbon leads to a twisted structure that avoids allylic conjugation. See: a) K. B. Wiberg, C. M. Breneman, T. J. LePage, J. Am. Chem. Soc. 1990, 112, 61.
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67650460053
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Naphthalene 5 was formed by olefin isomerization from intermediate F followed by dehydrative 1, 2-phenyl migration.
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Naphthalene 5 was formed by olefin isomerization from intermediate F followed by dehydrative 1, 2-phenyl migration.
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67650476808
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The preparation of corresponding starting materials (8b and 8c) is described in Supporting Information.
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The preparation of corresponding starting materials (8b and 8c) is described in Supporting Information.
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30
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67650488703
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Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
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Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
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