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For intramolecular oxonium ylide formation, see: (a) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060. (b) Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5603. (c) Clark, J. S.; Whitlock, G. A. Tetrahedron Lett. 1994, 35, 6381. (d) ref 23. (e) Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
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This is not always the requisite because free carbenes such as alkylidenecarbenes bearing a cyclic acetal ring also undergo a similar enlargement. See ref 13.
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46
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(b) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892.
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(c) West, F. G.; Eberlein, T. H.; Tester, R. W. J. Org. Chem. 1992, 57, 3479.
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48
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0343657876
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Reference 13
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(a) Reference 13.
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-
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49
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0342787638
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note
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(b) Unpublished results: The deuterium scrambling reaction of dithiolane-substituted diazocarbonyl compounds indicated that both intra- and intermolecular proton-transfer reactions can take place with bicyclic sulfonium ylides.
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51
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0343222224
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note
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When AcOH was used in place of MeOH, the reaction resulted in the formation of a complex mixture.
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52
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0006335945
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Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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Clark, J.S.1
Holmes, A.B.2
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53
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0021991255
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Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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Tetrahedron Lett.
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Asaoka, M.1
Naito, S.2
Takei, H.3
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54
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15844395902
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Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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J. Org. Chem.
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Asaki, M.1
Inoue, M.2
Tachibana, K.3
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55
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0025892697
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Other methods for preparing medium ring lactones by C-O bond formation: (a) Clark, J. S.; Holmes, A. B. Tetrahedron Lett. 1988, 34, 4333. (b) Asaoka, M.; Naito, S.; Takei, H. Tetrahedron Lett. 1985, 26, 2103. (c) Asaki, M.; Inoue, M.; Tachibana, K. J. Org. Chem. 1994, 59, 715. (d) Boger, D. L.; Sakya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
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J. Org. Chem.
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Boger, D.L.1
Sakya, S.M.2
Yohannes, D.3
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