オキシ-コープ転位
(oxy-Cope rearrangement から転送)
出典: フリー百科事典『ウィキペディア（Wikipedia）』 (2020/09/14 08:48 UTC 版)
有機化学において、オキシ-コープ転位（オキシ-コープてんい、英: Oxy-Cope rearrangement）は、化学反応の1つである。反応には特定の不飽和アルコールの骨格の再構成が含まれる。コープ転位のバリエーションであり、1,5-ジエン-3-オールが [3,3]-シグマトロピー転位に典型的な機構によって不飽和カルボニル化合物へと変換される[1][2]。
- ^ a b Berson, Jerome A.; Jones, Maitland (1964). “A Synthesis of Ketones by the Thermal Isomerization of 3-Hydroxy-1,5-hexadienes. The Oxy-Cope Rearrangement”. J. Am. Chem. Soc. 86 (22): 5019–5020. doi:10.1021/ja01076a067.
- ^ Cope, Arthur C.; Hardy, Elizabeth M. (1940). “The Introduction of Substituted Vinyl Groups. V. A Rearrangement Involving the Migration of an Allyl Group in a Three-Carbon System”. J. Am. Chem. Soc. 62 (2): 441–444. doi:10.1021/ja01859a055.
- ^ a b c d Paquette, Leo A. (1997). “Recent Applications of Anionic Oxy-Cope Rearrangements”. Tetrahedron 53 (41): 13971–14020. doi:10.1016/S0040-4020(97)00679-0.
- ^ a b c Kürti, Lázló; Czakó, Barbara (2005). Strategic Applications of Named Reactions in Organic Synthesis. Burlington: Elsevier Inc.. p. 325
- ^ a b Evans, D. A.; Golob, A. M. (1975). “[3,3]Sigmatropic Rearrangements of 1,5-Diene Alkoxides. The Powerful Accelerating Effects of the Alkoxide Substituent”. J. Am. Chem. Soc. 97 (16): 4765–4766. doi:10.1021/ja00849a054.
- ^ a b c Wilson, Stephen R. (1993). “Anion-Assisted Sigmatropic Rearrangements”. Org. React. 43 (2): 93–250. doi:10.1002/0471264180.or043.02.
- ^ Paquette, Leo A.; Ladouceur, Gaetan (1989). “Synthetic Studies Targeted at the Cytotoxic 8,9-Seco-ent-kaurene Diterpenes. Concise Complementary Stereocontrolled Construction of the Bridgehead Olefin Core”. J. Org. Chem. 54 (18): 4278–4279. doi:10.1021/jo00279a010.
- ^ Evans, D. A.; D. J., Baillargeon (1978). “Alkoxide Substituent Effects on Carbon—Carbon Bond Homolysis”. Tetrahedron Letters 19 (36): 3319–3322. doi:10.1016/S0040-4039(01)85627-6.
- ^ Paquette, Leo A.; Pierre, Francis; Cottrell, Charles E. (1987). “Anionic Rearrangements of syn- and anti-7-Cyclopentenyl-7-hydroxynorbornenes. The Case for Sequential Ring Cleavage and Intramolecular Michael Addition”. J. Am. Chem. Soc. 109 (19): 5731–5740. doi:10.1021/ja00253a027.
- ^ a b c d Maurin, Philippe; Kim, Se-Ho; Cho, Sung Yun; Cha, Jin Kun (2003). “On the Mechanism of the Anionic Oxy-Cope Rearrangement of trans-1,2-Dialkenylcyclobutanols”. Angew. Chem. 42 (41): 5044–5047. doi:10.1002/anie.200350988.
- ^ Evans, D. A.; Nelson, John V. (1980). “Stereochemical Study of the [3,3] Sigmatropic Rearrangement of 1,5-Diene-3-alkoxides. Application to the Stereoselective Synthesis of (±)-Juvabione”. J. Am. Chem. Soc. 102 (2): 774–782. doi:10.1021/ja00522a056.
- ^ Ogawa, Yasushi; Ueno, Tetsuya; Karikomi, Michinori; Seki, Katsura; Haga, Kazuo; Uyehara, Tadao (2001). “Synthesis of 2-Acetoxy[5]helicene by Sequential Double Aromatic Oxy-Cope Rearrangement”. Tetrahedron Lett. 43: 7827–7829. doi:10.1016/s0040-4039(02)01611-8.
- ^ Evans, D.A.; Baillargeon, D.J. (1978). “Intrinsic Fragmentation Modes of Primary Alkoxides”. Tetrahedron Lett. 19 (36): 3315–3318. doi:10.1016/S0040-4039(01)85626-4.
- ^ Baldwin, John E.; Black, Kersey A. (1984). “Complete Kinetic Analysis of Thermal Stereomutations among the Eight 2,3-Dideuterio-2-(methoxymethyl)spiro[cyclopropane-1,1'-indenes]”. J. Am. Chem. Soc. 106 (4): 1029–1040. doi:10.1021/ja00316a036.
- ^ Georges, Michael; Tam, Tim F.; Fraser-Reid, Bert (1985). “Controlled Access to Furanose Precursors Related to Sesquiterpene Lactones. 1”. J. Org. Chem. 50 (26): 5747–5753. doi:10.1021/jo00350a062.
- ^ Gadwood, Robert C.; Lett, Renee M. (1982). “Preparation and Rearrangement of 1,2-Dialkenylcyclobutanols. A Useful Method for Synthesis of Substituted Cyclooctenones”. J. Org. Chem. 47 (12): 2268–2275. doi:10.1021/jo00133a007.
- ^ Viola, Alfred; MacMillan, John H. (1970). “Vapor Phase Acetylenic Oxy-Cope Reaction of 5-Hexen-1-yn-3-ol. The Chemistry of an Allenol Intermediate”. J. Am. Chem. Soc. 92 (8): 2404–2410. doi:10.1021/ja00711a034.
- ^ Sworin, Michael; Lin, Ko Chung (1987). “Cyclopentanoid Synthesis via the Intramolecular Trapping of Oxy-Cope Intermediates. Stereocontrolled Synthesis of the cis- and trans-Hydroazulene Skeleton”. J. Org. Chem. 52 (25): 5640–5642. doi:10.1021/jo00234a029.
- ^ Macdonald, Timothy L.; Natalie, Kenneth J.; Prasad, Girija; Sawyer, J. Scott (1986). “Chemically Modified Potassium Hydride. Significant Improvement in Yields in Some Oxy-Cope Rearrangements”. J. Org. Chem. 51 (7): 1124–1126. doi:10.1021/jo00357a035.
- ^ Snowden, Roger L.; Muller, Bernard L.; Schulte-Elte, Karl H. (1981). “Fragmentation of Homoallylic Alkoxides. Synthesis of Propenyl and 2-Methylpropenyl Ketones from Carboxylic Esters”. Tetrahedron Lett. 23 (3): 335–338. doi:10.1016/S0040-4039(00)86824-0.
- ^ Evans, D. A.; Baillargeon, David J.; Nelson, John V. (1978). “A General Approach to the Synthesis of 1,6-Dicarbonyl Substrates. New Applications of Base-Accelerated Oxy-Cope Rearrangements”. J. Am. Chem. Soc. 100 (7): 2242–2244. doi:10.1021/ja00475a051.
[続きの解説]
「オキシ-コープ転位」の続きの解説一覧
- 1 オキシ-コープ転位とは
- 2 オキシ-コープ転位の概要
- 3 適用範囲
- oxy-Cope rearrangementのページへのリンク
