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A part of this work was published as preliminary communication: (a) Takasu, K.; Kuroyanagi, J.; Katsumata, A.; Ihara, M. Tetrahedron Lett. 1999, 40, 6277-6280.
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3242700108
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note
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-1 absorption (C=O) in IR spectrum (neat).
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31
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84970560674
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Previously, Curran depicted the radical reaction of analogous 1-iodo-1,5,10-triene. However, the reaction was unsatisfactory resulted in the production of tricyclo[6.3.0.0]undecane as an inseparable mixture of four diastereomers and another isomers. Curran, D. P.; Sun, S. Aust. J. Chem. 1995, 48, 261-267.
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Curran, D.P.1
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32
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3242677489
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note
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The reaction of tertiary alkyl radicals with intramolecular di- and tri-substituted olefin usually predominates 6-endo-trig cyclization over 5-exo-trig one. See ref. 3a.
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33
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33646230522
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In the second cyclization of 27, the rate of 5-exo-trig cyclization might be ∼100 times faster than 3-exo-trig cyclization, which can lead to homoallyl-homoallyl radical rearrangement. For a review of kinetics of radical cyclizations, see: Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323.
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Griller, D.1
Ingold, K.U.2
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