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Some interesting reviews on the synthesis of medium-sized cyclic ethers are:. Fujiwara K. In: Kiyota H. (Ed). Topics in Heterocyclic Chemistry Vol. 5 (2006), Springer, Berlin 97-148
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34250852077
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note
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For instance see Refs. 5c,f,j.
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41
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0035914520
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and references cited therein
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García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Lora Maroto B., and Díaz Morillo C. Tetrahedron Lett. 42 (2001) 8293 and references cited therein
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García Martínez, A.1
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de la Moya Cerero, S.4
Lora Maroto, B.5
Díaz Morillo, C.6
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42
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14044251506
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Cyclobutanes are frequent key structural units in biologically important compounds: For instance see:
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Cyclobutanes are frequent key structural units in biologically important compounds: For instance see:. Ortuño R.M., Moglioni G.Y., and Moltrasio G.Y. Curr. Org. Chem. 9 (2005) 237
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Ortuño, R.M.1
Moglioni, G.Y.2
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2042499683
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Xu F., Morikawa T., Matsuda H., Ninomiya K., and Yoshikawa M. J. Nat. Prod. 67 (2004) 569
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Xu, F.1
Morikawa, T.2
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Ninomiya, K.4
Yoshikawa, M.5
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45
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34250878774
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note
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1J(C-H) coupling constants (132-134 Hz).
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46
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1242307349
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The rate for the solvolysis of triflates via carbocationic processes can be improved using dimethyl sulfoxide as the solvent:
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The rate for the solvolysis of triflates via carbocationic processes can be improved using dimethyl sulfoxide as the solvent:. Creary X., and Burtch E.A. J. Org. Chem. 69 (2004) 1227
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J. Org. Chem.
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Creary, X.1
Burtch, E.A.2
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47
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34250813459
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note
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13C HMQC and selective 1D NOESY NMR experiments. Key dinstintive dipolar interactions are related with the C3-exo methyl and the C2 and C7 epoxidic methylene groups.
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48
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0036856586
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García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., and Lora Maroto B. Eur. J. Org. Chem. (2002) 3731
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Eur. J. Org. Chem.
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García Martínez, A.1
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García Fraile, A.3
de la Moya Cerero, S.4
Lora Maroto, B.5
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49
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0001693209
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Norbornane, bicyclo[2.1.1]heptane, cyclopentane, and cyclohexane are the common frameworks for products obtained by solvolysis of 1-norbornyl triflates. For instance, see:
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Norbornane, bicyclo[2.1.1]heptane, cyclopentane, and cyclohexane are the common frameworks for products obtained by solvolysis of 1-norbornyl triflates. For instance, see:. Müller P., Mareda J., and Milin D. J. Phys. Org. Chem. 8 (1995) 507
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Müller, P.1
Mareda, J.2
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50
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34250826874
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Olah G.A. (Ed), Wiley, New York Chapter 6
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Müller P., and Mareda J. In: Olah G.A. (Ed). Cage Hydrocarbons (1991), Wiley, New York Chapter 6
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Müller, P.1
Mareda, J.2
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51
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0028100613
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Also see:
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Also see:. García Martínez A., Osío Barcina J., Rodríguez Herrero M.E., Iglesias de Dios M., Teso Vilar E., and Subramanian L.R. Tetrahedron Lett. 35 (1994) 7285
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García Martínez, A.1
Osío Barcina, J.2
Rodríguez Herrero, M.E.3
Iglesias de Dios, M.4
Teso Vilar, E.5
Subramanian, L.R.6
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53
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0000496864
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Also see Ref. 7
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García Martinez A., Teso Vilar E., de la Moya Cerero S., Osío Barcina J., and Gómez P.C. J. Org. Chem. 64 (1999) 5611 Also see Ref. 7
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García Martinez, A.1
Teso Vilar, E.2
de la Moya Cerero, S.3
Osío Barcina, J.4
Gómez, P.C.5
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54
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note
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Ionization has been also proposed as the first step for the solvolysis of related spiroepoxide 1-norbornyl triflates (i.e., Ref. 7).
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55
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To the best of our knowledge no precedents have been reported for the formation of the interesting bicyclo[2.2.0]hexane system by rearrangement of 1-norbornyl cations. In this sense, see an unfortunate attempt in:
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To the best of our knowledge no precedents have been reported for the formation of the interesting bicyclo[2.2.0]hexane system by rearrangement of 1-norbornyl cations. In this sense, see an unfortunate attempt in:. Applequist D.E., and Klieman J.P. J. Org. Chem. 26 (1961) 2178
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(1961)
J. Org. Chem.
, vol.26
, pp. 2178
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Applequist, D.E.1
Klieman, J.P.2
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34250823282
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note
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Several reports have revealed that eight-membered rings are better formed if conformational restrictions imposed by an existing ring or other functional groups are present in the precursor (e.g., see Ref. 4b and references cited therein).
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34250865373
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Suzuki et al. have taken advantage of 8-exo-tet hydroxy epoxide cyclizations for the total syntheses of several interesting natural eight-membered cyclic ethers. For instance see Ref. 5a and references cited therein.
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Acid catalysis is probably acting in the process. A synchronous 7-to-9 step cannot be discarded.
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59
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34250847423
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note
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+{radical dot}, 20), 181 (5), 165 (13), 150 (13), 137 (23), 123 (24), 109 (29), 107 (31), 95 (100), 81 (48), 67 (48), 55 (36).
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C2-C3 rearrangement is the common observed process for related spiroepoxide 1-norbornyl triflates (Ref. 7).
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61
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34250875477
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note
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Note the undetected 6-exo-tet hydroxy-epoxide cyclization of 10, under the used reaction conditions, probably due to the unfavorable, and conformationally-restricted, disposition of both reacting groups.
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