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For examples of the coupling reactions of 2-lithio-1,3-dithiane with 2,3-disubstituted oxiranes, see: a) M. Nakata, H. Enari, and M. Kinoshita, Bull. Chem. Soc. Jpn., 55, 3283 (1982).
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0342931115
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For only one example of the coupling of 2-substituted 2-lithio-1,3-dithiane derivative with 2,3-disubstituted oxirane, see: a) F. Sher, J. L. Isidor, H. R. Taneja, and R. M. Carlson. Tetrahedron Lett., 1973, 577. For three examples of the coupling of 2-aryl- and 2-vinyl-stabilized 2-lithio-1,3-dithiane derivatives with 2,3-disubstituted oxiranes. see:
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A portion of this research has been preliminarily reported: M. Ide, M. Yasuda, and M. Nakata, Synlett, 1998, 936.
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85038134872
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The enantiomer of 9 was prepared by Smith et al., see Ref. 3h.
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30
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85038142413
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Besides them. 1-(triphenylmethoxy)-3-buten-2-ol was produced as a by-product derived from oxirane 22 in less than 5% yield.
-
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45
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85038145357
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note
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In the structures of 23, 24, 25, 26, 31, 32, and 33, Me and OH substituents originated from 22 are arranged to syn.
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47
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1542535886
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2Mg complex has been used, as a catalyst, for polymerization of monomers. For example, see: C. W. Kamienski, N. C. Gastonia, and J. F. Eastham, U. S. Patent 3847883 (1974); Chem. Abstr., 82, 58590 (1975).
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