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1H NMR spectra of the crude product mixtures with usual accuracy (≥±2%).
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A facile, though less stereoselective, formation of the corresponding cyclopentane derivatives from 2,6-dimethyl-5-hepten-1-al has also been observed.
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For the unlabeled product, see ref 41a and the following: Mori, K.; Umemura, T. Tetrahedron Lett. 1981, 22, 4429.
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Mori, K.1
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99
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0022499278
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For the unlabeled product, see refs 38a,b and the following: Patel, D. V.; Van Middlesworth, F.; Donaubauer, J.; Gannett, P.; Sih, C. J. J. Am. Chem. Soc. 1986, 108, 4603.
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Patel, D.V.1
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(b) Corey, E. J.; Yamamoto, H.; Herron, D. K.; Achiwa, K. J. Am. Chem. Soc. 1970, 92, 6635.
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For the method, see: Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618.
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Erickson, B.W.5
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108
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0344620904
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1H NMR spectrum
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1H NMR spectrum.
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109
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0013007401
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(a) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Wilson, T. M. Tetrahedron 1989, 45, 1053. See also:
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Denmark, S.E.1
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110
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(b) Thiyagarayan, B.; Michalczyk, L.; Bollinger, J. C.; Huffman, J. C.; Bruno, J. W. Organometallics 1996, 15, 1989 and references therein.
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Thiyagarayan, B.1
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112
-
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0345051527
-
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-1 energy difference between I and II/III (at room temperature)
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-1 energy difference between I and II/III (at room temperature).
-
-
-
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113
-
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0030748044
-
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Similar steric effect of a protruding CO ligand has been reported for the Diels-Alder addition of dienes to vinylmetallocarbenes, where it attenuates the secondary orbital interactions: Powers, T. S.; Jiang, W. Q.; Su, J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438-6439.
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(a) Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 9011.
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84903509973
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(b) Maruoka, K.; Saito, S.; Ooi, T.; Yamamoto, H. Synlett 1991, 579.
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Maruoka, K.1
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(c) Ooi, T.; Maruoka, K.; Yamamoto, H. Tetrahedron 1994, 50, 6505.
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Ooi, T.1
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117
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0344189243
-
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note
-
1-coordination).
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118
-
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0025280370
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2), see: Shambayati, S.; Crowe, W, E.; Schreiber, S. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 256.
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Shambayati, S.1
Crowe, W.E.2
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119
-
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0033557427
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2 coordination of an aldehyde group, see: Lenges, C. P.; Brookhart, M.; White, P. S. Angew. Chem., Int. Ed. 1999, 38, 552.
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Lenges, C.P.1
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White, P.S.3
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120
-
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0039959016
-
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This effect has been proposed to rationalize the predominant formation of the cis-product on cyclization cyclization of citronellal in micelles: Clark, B. C., Jr.; Chamblee, T.; Iacobucci, G. A. J. Org. Chem. 1984, 49, 4557.
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Clark, B.C.J.1
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121
-
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0345051526
-
-
note
-
2).
-
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122
-
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0039366726
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4a and 5a: (a) Nishimura, H.; Kaku, K.; Nakamura T.; Fukuzawa, Y.; Mizutani, J. Agric. Biol. Chem. 1982, 46, 319.
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Nishimura, H.1
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123
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0020423183
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(b) Nishimura, H.; Noma, Y.; Mizutani, J. Agric. Biol. Chem. 1982, 46, 2601.
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Nishimura, H.1
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124
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0041146103
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(c) Asakawa, Matsuda, R.; Tori, M.; Hashimoto, T. Phytochemistry 1988, 27, 386.
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Asakawa1
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0028134086
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(d) Takahashi, H.; Noma, Y., Toyota, M.; Ashakawa, Y. Phytochemistry 1994, 35, 1465. 4a:
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Takahashi, H.1
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0000696586
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(e) Stein, D.; Sam, R.; Nouguier, B.; Crich, D.; Bertrand, M. P. J. Org. Chem. 1997, 62, 275.
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Stein, D.1
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127
-
-
0344620900
-
-
note
-
1H NMR. Thus, 5a, with an axial OH, shows the proton in question as a broad doublet (J = 2.5 Hz), whereas the equatorial epimer 4a exhibits a dt with J = 10.5 and 4.3 Hz.
-
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-
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128
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0001370993
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(a) Crandall, J. K.; Arrington, J. P.; Hen, J. J. Am. Chem. Soc. 1967, 89, 6208 and 6212.
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Crandall, J.K.1
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0040551993
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Cope, A.C.1
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33845374531
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(c) Hendrickson, J. B.; Boudreaux, G. J.; Palumbo, P. S. J. Am. Chem. Soc. 1986, 108, 2358.
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Hendrickson, J.B.1
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37049111988
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(b) Kirby, G. W.; McGuigan, H.; McLean, D. J. Chem. Soc., Perkin Trans. 1 1986, 1961.
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Kirby, G.W.1
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0000665529
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(b) Hibino, J. I.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579.
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Hibino, J.I.1
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139
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0041146102
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van den Heuevel, W. J. A.; Wallis, E. S. J. Org. Chem. 1962, 27, 1233. For the cis-isomer, see: Julia, S.; Julia, M.; Brasseur, L. Bull. Soc. Chim. Fr. 1962, 374.
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Van Den Heuevel, W.J.A.1
Wallis, E.S.2
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140
-
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0039366725
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van den Heuevel, W. J. A.; Wallis, E. S. J. Org. Chem. 1962, 27, 1233. For the cis-isomer, see: Julia, S.; Julia, M.; Brasseur, L. Bull. Soc. Chim. Fr. 1962, 374.
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Julia, S.1
Julia, M.2
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142
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0039366724
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(b) D'Incan, E.; Loupy, A.; Maia, A.; Seyden-Penne, J.; Vitout, P. Tetrahedron 1982, 38, 2923.
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Tetrahedron
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D'Incan, E.1
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144
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0026632630
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Shishido, K.; Irie, O.; Shibuya, M. Tetrahedron Lett. 1992, 33, 4589.
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Shishido, K.1
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146
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37049166938
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Attenburrow, A.; Cameron, A. F. B.; Chapman, J. H.; Evans, R. M.; Hems, B. A.; Jansen, A. B. A.; Walker, T. J. Chem. Soc. 1952, 1094.
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Attenburrow, A.1
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Walker, T.7
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147
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37049076905
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For the unlabeled product, see: Inoue, S.; Kaneko, T.; Takahashi, Y.; Miyamoto, O.; Sato, K. J. Chem. Soc., Chem. Commun. 1987, 1036.
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Sato, K.5
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