乙烯基环丙烷重排反应 (Chinese Wikipedia)

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  • Hudlicky, Tomas; Reed, Josephine W. From Discovery to Application: 50 Years of the Vinylcyclopropane-Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products. Angewandte Chemie International Edition. 2010, 49 (29): 4864–76. PMID 20586104. doi:10.1002/anie.200906001. 
  • Woodworth, Robert C.; Skell, Philip S. Reactions of bivalent carbon species. Addition of dihalocarbenes to 1,3-butadiene. J. Am. Chem. Soc. 1957, 79 (10): 2542. doi:10.1021/ja01567a048. 
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  • Neureiter, Norman. Pyrolysis of 1,l-Dichloro-2-vinylcyclopropane. Synthesis of 2-Chlorocyclopentadiene. J. Org. Chem. 1959, 24 (12): 2044. doi:10.1021/jo01094a621. 
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  • Overberger, C. G.; Borchert, A. E. Ionic Polymerization. XVI. Reactions of 1-Cyclopropylethanol-Vinylcyclopropane. J. Am. Chem. Soc. 1960, 82 (18): 4896. doi:10.1021/ja01503a036. 
  • Doering, W. von E.; Lambert, J. B. Thermal Reorganization of a- and b-Thujene: A degenerate rearrangement of the vinylcyclopropane type. Tetrahedron. 1963, 19 (12): 1989. doi:10.1016/0040-4020(63)85013-9. 
  • Atkinson, R. S.; Rees, C. W. A vinylaziridine to pyrroline rearrangement. Chemical Communications (London). 1967, (23): 1232a. doi:10.1039/C1967001232a. 
  • Lwowski, Walter; Rice, Susan N.; Lwowski, Walter. Singlet and Triplet Nitrenes. 111. The Addition of Carbethoxynitrene to 1,3-Dienes. J. Org. Chem. 1968, 33 (22): 481. doi:10.1021/jo01266a001. 
  • Paladini, J; Chuche, X. X. Rearrangement thermique d'epoxydes vinyliques. Tetrahedron Letters. 1971, 12 (46): 4383. doi:10.1016/S0040-4039(01)97447-7. 
  • Demjanow, N. J.; Dojarenko, Marie. Über Vinylcyclopropan, einige Derivate des Methyl-cyclopropyl-carbinols und die Isomerisation des Cyclopropan-Ringes. Ber. Dtsch. Chem. Ges. B. 1922, 55 (8): 2718 [2021-12-07]. doi:10.1002/cber.19220550846. (原始内容存档于2021-12-07). 
  • Cloke, J. B.; Borchert, A. E. The formation of pyrrolines from gamma-chloropropyl and cyclopropyl ketimines. J. Am. Chem. Soc. 1929, 51 (18): 1174. doi:10.1021/ja01379a028. 
  • Wilson, C. L.; Borchert, A. E. Reactions of Furan Compounds. VII. Thermal Interconversionof 2,3-Dihydrofuran and Cyclopropane Aldehyde. J. Am. Chem. Soc. 1947, 69 (18): 3002. doi:10.1021/ja01204a020. 
  • Baldwin, John E. Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes. Chemical Reviews. 2003, 103 (4): 1197–212. PMID 12683781. doi:10.1021/cr010020z. 
  • Flowers, M. C.; Rabinovitch, B. S. The Thermal Unimolecular Isomerisation of Vinylcyclo- propane to Cyclopentene. J. Chem. Soc. 1960, 82 (23): 3547. doi:10.1021/ja01508a008. 
  • Schlag, E. W.; Rabinovitch, B. S. Kinetics of the Thermal Unimolecular Isomerization Reactions of Cyclopropane-d2. J. Am. Chem. Soc. 1960, 82 (23): 5996. doi:10.1021/ja01508a008. 
  • Egger, K. W.; Golden, David M.; Benson, Sidney W. Iodine-Catalyzed Isomerization of Olefins. 11. The Resonance Energy of the Allyl Radical and the Kinetics of the Positional Isomerization of 1-Butene. J. Am. Chem. Soc. 1964, 86 (24): 5420. doi:10.1021/ja01078a011. 
  • Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry. Angew. Chem. Int. Ed. 1969, 8 (11): 781. doi:10.1002/anie.196907811. 
  • Gajewski, Joseph J.; Squicciarini, Michael P. Evidence for concert in the vinylcyclopropane rearrangement. A reinvestigation of the pyrolysis of trans-1-methyl-2-(1-tert-butylethenyl)cyclopropane. Journal of the American Chemical Society. 1989, 111 (17): 6717. doi:10.1021/ja00199a035. 
  • Gajewski, Joseph J.; Olson, Leif P. Evidence for a dominant suprafacial-inversion pathway in the thermal unimolecular vinylcyclopropane to cyclopentene 1,3-sigmatropic shift. Journal of the American Chemical Society. 1991, 113 (19): 7432. doi:10.1021/ja00019a056. 
  • Gajewski, Joseph J.; Olson, Leif P.; Willcott, M. Robert. Evidence for Concert in the Thermal Unimolecular Vinylcyclopropane to Cyclopentene Sigmatropic 1,3-Shift. Journal of the American Chemical Society. 1996, 118 (2): 299. doi:10.1021/ja951578p. 
  • Corey, E. J.; Walinsky, S. W. Reaction of 1,3-dithienium fluoroborate with 1,3-dienes. Synthesis of .DELTA.3-cyclopenten-1-ones. Journal of the American Chemical Society. 1972, 94 (25): 8932. doi:10.1021/ja00780a063. 
  • Simpson, John M.; Richey, Herman G. The effects of methoxyl and phenyl substituents on the thermal rearrangements of vinylcyclopropane. Tetrahedron Letters. 1973, 14 (27): 2545. doi:10.1016/S0040-4039(01)96201-X. 
  • Trost, Barry M.; Bogdanowicz, Mitchell J. New synthetic reactions. IX. Facile synthesis of oxaspiropentanes, versatile synthetic intermediates. Journal of the American Chemical Society. 1973, 95 (16): 5311. doi:10.1021/ja00797a036. 
  • Trost, Barry M.; Keeley, Donald E. New synthetic methods. A stereocontrolled approach to cyclopentane annelation. Journal of the American Chemical Society. 1976, 98: 248–250. doi:10.1021/ja00417a048. 
  • Paquette, Leo A.; Meehan, George V.; Henzel, Richard P.; Eizember, Richard F. Photochemistry of conjugated cis-bicyclo[5.1.0]octenones, cis- and trans-bicyclo[5.2.0]non-2-en-4-ones, and their methylene analogs. The Journal of Organic Chemistry. 1973, 38 (19): 3250. doi:10.1021/jo00959a004. 
  • Paquette, Leo A.; Henzel, Richard P.; Eizember, Richard F. Thermochemical behavior of conjugated cis-bicyclo[5.1.0]octenones, cis- and trans-bicyclo[5.2.0]non-2-en-4-ones, and their methylene analogs. The Journal of Organic Chemistry. 1973, 38 (19): 3257. doi:10.1021/jo00959a005. 
  • Hudlicky, Tomas; Koszyk, Francis F.; Kutchan, Toni M.; Sheth, Jagdish P. Cyclopentene annulation via intramolecular addition of diazoketones to 1,3-dienes. Applications to the synthesis of cyclopentanoid terpenes. The Journal of Organic Chemistry. 1980, 45 (25): 5020. doi:10.1021/jo01313a003. 
  • Brown, Vanessa; Brown, John M.; Conneely, John A.; Golding, Bernard T.; Williamson, David H. Synthesis and thermolysis of rhodium and iridium complexes of endo-6-vinylbicyclo[3.1.0]hex-2-ene. A metal-promoted vinylcyclopropane to cyclopentene rearrangement. Journal of the Chemical Society, Perkin Transactions 2. 1975, (1): 4. doi:10.1039/P29750000004. 
  • Danheiser, Rick L.; Martinez-Davila, Carlos; Morin, John M. Synthesis of 3-cyclopentenols by alkoxy-accelerated vinylcyclopropane rearrangement. The Journal of Organic Chemistry. 1980, 45 (7): 1340. doi:10.1021/jo01295a045. 
  • Larsen, Scott D. A stereoselective synthesis of functionalized cyclopentenes via base-induced ring contraction of thiocarbonyl Diels-Alder adducts. Journal of the American Chemical Society. 1988, 110 (17): 5932–5934. doi:10.1021/ja00225a072. 
  • Hudlicky, Tomas; Heard, Nina E.; Fleming, Alison. 4-Siloxy-.alpha.-bromocrotonate: A new reagent for [2+3] annulation leading to oxygenated cyclopentenes at low temperatures. The Journal of Organic Chemistry. 1990, 55 (9): 2570. doi:10.1021/jo00296a004. 
  • Trost, B. M.; Nishimura, Yoshio; Yamamoto, Kagetoshi. A Total Synthesis of Aphidicolin. J. Am. Chem. Soc. 1979, 101 (5): 1328. doi:10.1021/ja00499a071. 
  • Piers, E. Five-membered Ring Annelation via Thermal Rearrangement of a-Cyclopropyl-ab-unsaturated Ketones: a New Total Synthesis of (&)-Zizaene. J. Chem. Soc. Chem. Commun. 1979, (24): 1138. doi:10.1039/C39790001138. 
  • Hudlicky, T.; Kutchan, Toni M.; Wilson, Stephen R.; Mao, David T. Total Synthesis of (rac)-Hirsutene. J. Am. Chem. Soc. 1980, 102 (20): 6351. doi:10.1021/ja00540a036. 
  • Hudlicky, T.; Kavka, Misha; Higgs, Leslie A.; Hudlickyl, Tomas. Stereocontrolled Total Synthesis of Isocomene Sesquiterpenes. Tetrahedron Lett. 1984, 25 (23): 2447. doi:10.1016/S0040-4039(01)81201-6. 
  • Paquette, L. A. A Short Synthesis of (rac)-alpha-Vetispirene. Tetrahedron Lett. 1982, 23: 3227. doi:10.1016/s0040-4039(00)87576-0. 
  • Corey, E. J.; Myers, Andrew G. Total Synthesis of (rac)-Antheridium-Inducing Factor (AAn,2) of the Fern Anemia pbylfitidis. Clarification of Stereochemistry. J. Am. Chem. Soc. 1985, 107 (19): 5574. doi:10.1021/ja00305a067. 
  • Njardarson, J. T.; Araki, H; Batory, LA; McInnis, CE; Njardarson, JT. Highly Selective Copper-Catalyzed Ring Expansion of Vinyl Thiiranes: Application to Synthesis of Biotin and the Heterocyclic Core of Plavix. J. Am. Chem. Soc. 2007, 129 (10): 2768–9. PMID 17302422. doi:10.1021/ja069059h. 
  • Majetich, G.; Zou, G; Grove, J. Total Synthesis of (−)-Salviasperanol. Org. Lett. 2008, 10 (1): 85–7. PMID 18052176. doi:10.1021/ol701743c. 

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  • Hudlicky, Tomas; Reed, Josephine W. From Discovery to Application: 50 Years of the Vinylcyclopropane-Cyclopentene Rearrangement and Its Impact on the Synthesis of Natural Products. Angewandte Chemie International Edition. 2010, 49 (29): 4864–76. PMID 20586104. doi:10.1002/anie.200906001. 
  • Baldwin, John E. Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes. Chemical Reviews. 2003, 103 (4): 1197–212. PMID 12683781. doi:10.1021/cr010020z. 
  • Njardarson, J. T.; Araki, H; Batory, LA; McInnis, CE; Njardarson, JT. Highly Selective Copper-Catalyzed Ring Expansion of Vinyl Thiiranes: Application to Synthesis of Biotin and the Heterocyclic Core of Plavix. J. Am. Chem. Soc. 2007, 129 (10): 2768–9. PMID 17302422. doi:10.1021/ja069059h. 
  • Majetich, G.; Zou, G; Grove, J. Total Synthesis of (−)-Salviasperanol. Org. Lett. 2008, 10 (1): 85–7. PMID 18052176. doi:10.1021/ol701743c. 

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