Метилэтилдиоксиран и 1, 2-диокса-спиро[2.5]октан.
Термическая стабильность и реакционная способность
Диссертация
Изучены продукты и кинетика термического распада метилэтилдиоксирана и 1,2-диоксаспирооктана. Термический распад изученных диоксиранов протекает по трем направлениям: изомеризация в сложные эфиры, внедрение атома кислорода по С-Н связи растворителя, отрыв атома водорода от молекулы растворителя. Доля радикального канала реакции при 35 °C составляет 0.43 и 0.29 для метилэтилдиоксирана… Читать ещё >
Содержание
- 1. ОБЗОР ЛИТЕРАТУРЫ
- 1. 1. СТРУКТУРА И СПЕКТРАЛЬНЫЕ ХАРАКТЕРИСТИКИ ДИОКСИРАНОВ
- 1. 2. МЕТОДЫ СИНТЕЗА ДИОКСИРАНОВ
- 1. 2. 1. Окисление диалкоксидов
- 1. 2. 2. Озонолиз ненасыщенных соединений и кетонов
- 1. 2. 3. Низкотемпературное фотоокисление диазосоединений
- 1. 2. 4. Пероксидный метод
- 1. 2. 5. Другие примеры синтеза диоксиранов
- 1. 3. РАСПАД ДИОКСИРАНОВ
- 1. 3. 1. Диоксиран
- 1. 3. 2. Метил (трифторметил)диоксиран
- 1. 3. 3. 1,2-Диокса-спиро[2.5]октан
- 1. 3. 4. Димезитилдиоксиран
- 1. 3. 5. Диметилдиоксиран
- 1. 4. РЕАКЦИИ ДИОКСИРАНОВ С ОРГАНИЧЕСКИМИ СОЕДИНЕНИЯМИ
- 1. 4. 1. Окисление С-Н связей насыщенных соединений диоксиранами
- 1. 4. 2. Взаимодействие спиртов с диоксиранами
- 1. 4. 3. Окисление эфиров
- 2. 1. СИНТЕЗ И ОЧИСТКА РЕАГЕНТОВ
- 2. 1. 1. Очистка реактивов
- 2. 1. 3. Синтез диметилдиоксирана и метилэтилдиоксирана
- 2. 1. 4. Синтез 1,2-диокса-спиро[2.5]октана
- 2. 2. МЕТОДЫ АНАЛИЗА
- 2. 2. 1. ЯМР анализ
- 2. 2. 2. Хроматографический анализ
- 2. 2. 3. Масс-спектрометрические измерения
- 2. 2. 4. Анализ метилэтилдиоксирана и 1,2-диокса-спиро[2.5]октана
- 2. 3. МЕТОДИКА КИНЕТИЧЕСКОГО ЭКСПЕРИМЕНТА
- 2. 3. 1. Спектрофотометрический метод
- 2. 3. 2. Определение концентрации кислорода в жидкой фазе
- 3. 1. ТЕРМИЧЕСКИЙ РАСПАД МЕТИЛЭТИЛДИОКСИРАНА
- 3. 1. 1. Продукты распада метилэтилдиоксирана
- 3. 1. 2. Кинетические закономерности термолиза метил-этилдиоксирана в атмосфере кислорода
- 3. 1. 3. Механизм процесса
- 3. 1. 4. Квантово-химические расчеты
- 3. 2. ТЕРМИЧЕСКИЙ РАСПАД 1,2-ДИОКСА-СПИРО[2.5]ОКТАНА
- 3. 2. 1. Продукты распада 1,2-диокса-спиро[2.5]октана
- 3. 2. 2. Кинетика термолиза 1,2-диокса-спиро[2,5]октанав атмосфере кислорода
- 3. 2. 3. Механизм процесса
- 3. 3. РЕАКЦИОННАЯ СПОСОБНОСТЬ МЕТИЛЭТИЛДИОКСИРАНА, ДИМЕТИЛДИОКСИРАНА И 1,2-ДИОКСА-СПИРО[2.5]ОКТАНА
- 3. 3. 1. Окисление спиртов метилэтилдиоксираном и 1,2-диокса-спиро[2.5]октаном
- 3. 3. 2. Окисление простых эфиров метилэтилдиоксираном и 1,2-диокса-спиро[2.5]октаном
- 3. 3. 3. Окисление углеводородов диметилдиоксираном, метилэтилдиоксираном и 1,2-диокса-спиро[2.5]октаном
Список литературы
- Д.В. Казаков, А. И. Волошин, В. П. Казаков, В. В. Шерешовец, Н. Н. Кабальнова, Химия и хемшюминесценг^ш диоксиранов. Москва, «Наука», 1999, 165 с.
- R.I. Talbott, P.G. Thompson, Fluorinated Organic Cyclic Peroxides. US Patent 3 632 606, 1972.
- H.-O. Kalinowski, In Struktur Von Peroxo-Verbindungen In Houben-Weyl. Vol. E13. Stuttgart, 1988.
- R.D. Suenram, F.J. Lovas, Dioxirane Its Synthesis, Microwave-Spectrum,
- Structure, and Dipole-Moment IIJ. Am. Chem. Soc. 1978. — V.100. — № 16. -P.5117−5122.
- H. Burger, P. Weinrath, G.A. Arguello, B. Julicher, H. Willner, D.D. Desmarteau, A. Russo, the High-Resolution Midinfrared Ft Spectrum of
- Difluorodioxirane CF202 the Ground, Nu (l), Nu (2) and Nu (8) States //J.
- Mol. Spectrosc. 1994. — V.168. — № 2. — P.607−620.
- B. Casper, D. Christen, H.G. Mack, H. Oberhammer, G.A. Arguello, B. Julicher, M. Kronberg, H. Willner, Electron Diffraction and Vibrational Spectra of Difluorodioxirane, CF202 HJ. Phys. Chem. 1996. — V.100. -№ 10. — P.3983−3988.
- E. Kraka, Z. Konkoli, D. Cremer, J. Fowler, H.F. Schaefer, Difluorodioxirane: An Unusual Cyclic Peroxide HJ. Am. Chem. Soc. 1996. — V. U8.-№ 43.-P.10 595−10 608.
- W. Adam, Y.Y. Chan, D. Cremer, J. Gauss, D. Scheutzow, M. Schindler, Spectral and Chemical-Properties of Dimethyldioxirane As Determined by Experiment and Abinitio Calculations HJ. Org. Chem. 1987. — V.52. — № 13.- P.2800−2803.
- D. Cremer, M. Schindler, Energy, Geometry and Nmr Chemical-Shifts of Dimethyldioxirane //Chem. Phys. Lett. 1987. — V.133. — № 4. — P.293−297.
- D. Cremer, E. Kraka, P.G. Szalay, Decomposition Modes of Dioxirane, Methyldioxirane and Dimethyldioxirane a CCSD (T), MR-AQCC and DFT Investigation //Chem. Phys. Lett. — 1998. — V.292. — № 1−2. — P.97−109.
- S.J. Kim, H.F. Schaefer, Dimethyldioxirane, Carbonyl Oxide, and the Transition State Connecting Them: Electronic Structures, Relative Energies, And Vibrational Frequencies. HJ. Phys. Chem. a 2000. — V.104. — № 33. -P.7892−7897.
- W.W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, Dimesityldioxirane //J. Am. Chem. Soc. 1997. — V. 119. — № 31. — P.7265−7270.
- R.W. Murray, R. Jeyaraman, Dioxiranes: Synthesis and Reactions of Methyldioxiranes HI Org. Chem. 1985. — V.50. — № 16. — P.2847−2853.
- R.W. Murray, Chemistry of Dioxiranes .12. Dioxiranes HChem. Rev. 1989.- V.89. № 5. — P.1187−1201.
- R. Mello, M. Fiorentino, O. Sciacovelli, R. Curci, On the Isolation and Characterization of Methyl (Trifluoromethyl)Dioxirane //,/. Org. Chem. -1988. V.53. — № 16. — P.3890−3891.
- R.W. Murray, M. Singh, R. Jeyaraman, Dioxiranes .20. Preparation and Properties of Some New Dioxiranes HJ. Am. Chem. Soc. 1992. — V.114. -№ 4. — P.1346−1351.
- K.R. Kopecky, X. Yu, J. Molina, Dioxirane Formation In Ozonolysis of E-l, 2-Dimethoxy-l, 2- Diphenylethene and Z-l, 2-Dimethoxy-l, 2-Diphenylethene IICan. J. Chem.-Rev. Can. Chim. 1993. — V.71. — № 2. -P.272−274.
- F.J. Lovas, R.D. Suenram, Identification of Dioxirane (PI2coo) In Ozone-Olefin Reactions Via Microwave Spectroscopy I I Chem. Phys. Lett. 1977. -V.51. — № 3. — P.453−456.
- R.I. Martinez, R.E. Huie, J.T. Herron, Mass-Spectrometric Detection of Dioxirane, H2COO, and Its Decomposition Products, H-2 and Co, From Reaction of Ozone With Ethylene 11 Chem. Phys. Lett. 1977. — V.51. — № 3. -P.457−459.
- S.A. Kafafi, R.I. Martinez, J.T. Herron, Chemistry of Dioxymethylenes and Dioxiranes HMol. Struct. Energ. 1988. — V.6. — № 2. — P.283−310.
- T.A. Walter, J.J. Bufalini, B.W.J. Gay, Mechanism for Olefin-Ozone Reactions IIEnviron. Res. Cent. 1977. — V.ll. — № 4. — P.382−386.
- H.E. O’Neal, C. Blumstein, New Mechanism for Gas-Phase Ozone-Olefm Reactions Hint. J. Chem. Kinet. 1973. — V.5. — № 3. — P.397−413.
- S. Vaccani, H. Kuhne, A. Bauder, H.H. Gunthard, Infrared Matrix and Microwave Spectroscopy On the Gas Phase Vinylchloride-Ozone Reaction l/Chem. Phys. Lett. 1977. — V.50. — № 2. — P.187−189.
- R.E. Keay, G.A. Hamilton, Alkene Epoxidation by Intermediates Formed During the Ozonation of Alkynes HJ. Am. Chem. Soc. 1976. — V.98. — № 21. — P.6578−6582.
- W.A. Pryor, C.K. Govindan, D.F. Church, Mechanism of Ozonolysis of Acetylenes: Evidence for a Free-Radical Pathway for the Decomposition of Intermediates IIJ. Am. Chem. Soc. 1982. — V.104. — № 26. — P.7563−7566.
- R.FI. Eastman, R.M. Silverestein, Anomalies In the Vapor Phase Ozonolysis of Cyclohexene HJ. Am. Chem. Soc. 1953. — V.75. — № 6. — P.1493−1494.
- H.E. Smith, R.FI. Eastman, the Vapor Phase Reaction of 2,3-Dimethyl-2-Butene and Ozone HJ. Am. Chem. Soc. 1961. — V.83. — № 20. — P.4293−4276.
- B.J. Finlayson, J.N. Pitts, R. Atkinson, Low-Pressure Gas-Phase Ozone-Olefin Reactions. Cemiluminescence, Kinetics, and Mechanisms HJ. Am. Chem. Soc. 1974. — V.96. — № 17. — P.5356−5367.
- W.W. Sander, A. Kirschfeld, Advances In Strain In Organic Chemistry. Vol 4. London, JAI Press Inc., 1995.
- W.W. Sander, Carboniloxide: Zwitterionen Oder Diradikale? IIAngew. Chem. 1990. — V.102. — № 4. — P.362−372.
- O.L. Chapman, T.C. Hess, Cyclopentadienone O-Oxides: Spectroscopic Observation and Photochemistry of a Carbonyl Oxide IIJ. Am. Chem. Soc. -1984. V.106. — № 6. — P.1842−1843.
- G.A. Bell, I.R. Dunkin, Cyclopentadienone O-Oxide: a Highly Labile Intermediate In the Matrix Reaction Between Cyclopentadienylidene and Oxygen. HJ. Chem. Soc., Chem. Commun. 1983. — № 21. — P.1213−1215.
- G.A. Bell, I.R. Dunkin, C.J. Shields, Matrix Electronic Absorption Spectra On the Adducts of 02 With Cyclopentadienylidene, Tetrachlorocyclopentadienylidene, Indenylidene and Fluorenylidene l/Spectrochim. Acta 1985. — V.41A. — № 10. — P.1221−1227.
- I.R. Dunkin, G.A. Bell, the Generation and Photochemistry of Indenone 0-Oxide and Fluorenone O-Oxide In Low Temperature Matrices //Tetrahedron 1985. — V.41. — № 2. — P.339−347.
- I.R. Dunkin, C.J. Shields, the Photo-Isomerization of Cyclopentadienone 0-Oxide Isolated In Low Temperature Matrices HJ. Chem. Soc., Chem. Commun. 1986. — № 2. — P.154−156.
- W.W. Sander, Benzophenon 0 Oxid HAngew. Chem. 1986. — V.98. — № 3. -P.255−256.
- W. Sander, A. Kirschfeld, S. Muthusamy, K. Schroeder, W. Kappert, Photochemical Synthesis of Novel Oxygen Transfer Reagents IIJ. Inform. Rec. 1998. — V.24. — № 5−6. — P.349−356.
- W.W. Sander, Reaktion Von Phenylcarben Mit Sauerstoff IIAngew. Chem. -1985. V.97. — № 11. — P.964−965.
- W.W. Sander, Effects of Electron-Withdrawing Groups On Carbonyl 0-Oxides. Trifluoroacetophenone O-Oxide and Hexafluoroacetone O-Oxide IIJ. Org. Chem. 1988. — V.53. — № 1. — P.121−126.
- G.A. Ganzer, R.S. Sheridan, M.T.H. Liu, Reaction of Phenylchlorocarbene In Oxygen-Doped Matrices HJ. Am. Chem. Soc. 1986. — V.108. — № 7. -P.1517−1520.
- W.W. Sander, P-Benzoquinone O-Oxide HJ. Org. Chem. 1988. — V.53. -№ 9. — P.2091−2093.
- W.W. Sander, Chemiluminescence From Arylcarbene Oxidation: Phenylchloro’carbene and (2-Chlorophenyl)Carbene HSpectrochim. Acta. -1987. V.43A. — № 5. — P.637−646.
- G. Bucher, W. Sander, Carbonyl O-Oxides and Dioxiranes the Influence of Substituents On Spectroscopic Properties 11 Chem. Ber.-Recl. — 1992. -V.125. — № 8. — P.1851−1859.
- A. Kirschfeld, S. Muthusamy, W. Sander, Dimesityldioxiran Ein In Substanz Stabiles Dioxiran IIAngew. Chem. 1994. — V.106. — № 21. -P.2261−2263.
- R.E. Montgomery, Catalysis of Peroxymonosulfate Reactions by Ketones HJ. Am. Chem. Soc. 1974. — V.96. — № 25. — P.7820−7821.
- J.O. Edwards, R.H. Pater, R. Curci, F. Difuria, Formation and Reactivity of Dioxirane Intermediates In the Reaction of Peroxoanions With Organic Substrates HPhotochem. Photobiol. 1979. — V.30. — № 1. — P.63−70.
- R. Curci, M. Fiorentino, L. Troisi, J.O. Edwards, R.H. Pater, Epoxidation of Alkenes by Dioxirane Intermediates Arising In the Reaction of Potassium Caroate With Ketones HAbstr. Pap. Am. Chem. Soc. 1980. — V.180. -№AUG. — P.224-ORGN.
- R. Curci, M. Fiorentino, L. Troisi, J.O. Edwards, R.H. Pater, Epoxidation of Alkenes by Dioxirane Intermediates Generated In the Reaction of Potassium Caroate With Ketones HJ. Org. Chem. 1980. — V.45. — № 23. — P.4758−4760.
- A.R. Gallopo, J.O. Edwards, Kinetics and Mechanism of the Oxidation of Pyridine by Caro’s Acid Catalyzed by Ketones HJ. Org. Chem. 1981. -V.46. — № 8. — P.1684−1688.
- R. Curci, M. Fiorentino, M.R. Serio, Asymmetric Epoxidation of Unfunctionalized Alkenes by Dioxirane Intermediates Generated From Potassium Peroxomonosulphate and Chiral Ketones IIJ. Chem. Soc.-Chem. Commun. 1984. — № 3. — P.155−156.
- L. Cassidei, M. Fiorentino, R. Mello, 0. Sciacovelli, R. Curci, 0−17 and C-13 Identification of the Dimethyldioxirane Intermediate Arising In the Reaction of Potassium Carbonate With Acetone IIJ. Org. Chem. 1987. -V.52. — № 4. — P.699−700.
- W. Adam, J. Bialas, L. Hadjiarapoglou, a Convenient Preparation of Acetone Solutions of Dimethyldioxirane HChem. Berichte 1991. — V.124. -№ 10.-P.2377.
- M. Schulz, S. Liebsch, R. Kluge, W. Adam, Organo Sulfonic Peracids .4. the Reaction of Arenesulfonylimidazoles With H202 In the Presence of Ketones, a New Entry to Dioxiranes IIJ. Org. Chem. 1997. — V.62. — № 1. -P.188−193.
- A. Russo, D.D. Desmarteau, Difluorodioxirane IIAngew. Chem. 1993. -V.105. — № 6. — P.956−958.
- W. Ando, H. Miyazaki, S. Kohmoto, Oxygen Atom Transfer by An Intermediate In the Photosensitized Oxygenation of Diazo Compounds //Tetrahedron Lett. 1979. — V.20. — № 15. — P. 1317−1320.
- W. Ando, R. Sato, Ii. Sonobe, T. Akasaka, Reaction of Singlet Oxygen With Azines Implications for Dioxirane Intermediate I/Tetrahedron Lett — 1984. — V.25. — № 8. — P.853−856.
- A. Sekiguchi, Y. Kabe, W. Ando, Dye-Sensitized Photo oxidation of Silyl Diazo Compounds. Intramolecular Oxygen Transfer of Carbonyl Oxides HJ. Org Chem. 1982. — V.47. — № 15. — P.2900−2903.
- W. Adam, R. Curci, M.E.G. Nunez, R. Mello, Thermally and Photochemically Initiated Radical Chain Decomposition of Ketone-Free Methyl (Trifluoromethy 1) D ioxirane HJ. Am. Chem. Soc. 1991. — V.113. -№ 20. — P.7654−7658.
- M. Singh, R.W. Murray, Chemistry of Dioxiranes .21. Thermal-Reactions of Dioxiranes HJ. Org. Chem. 1992. — V.51. — № 15. — P.4263−4270.
- A.L. Baumstark, M. Beeson, P.C. Vasquez, Dimethyldioxirane Mechanism of Benzaldehyde Oxidation //Tetrahedron Lett. — 1989. — V.30. — № 41. -P.5567−5570.
- J. Bouchard, C. Maine, R.M. Berry, D.S. Argyropoulos, Kraft Pulp Bleaching Using Dimethyldioxirane: Stability of the Oxidants //Can. J. Chem.-Rev. Can. Chim. 1996. — V.74. — № 2. — P.232−237.
- F.H. Gorth, Oxidation Von 1,2,4-Triazinen Und Diazinen Mit Dioxiranen. Wurzburg, Diplomarbeit, 1996.
- W. Adam, F. Prechtl, Highly Efficient Hydroxylation of Carbonyl-Compounds With Dimethyldioxirane I I Chem. Berichte 1991. — V.124. -№ 10. — P.2369−2372.
- L.A. Hull, L. Budhai, Thermal-Decomposition of Dimethyldioxirane //Tetrahedron Lett. 1993. — V.34. — № 32. — P.5039−5042.
- L. Budhai, L.A. Hull, Thermal-Decomposition of Dimethyldioxirane IIAbstr. Pap. Am. Chem. Soc. 1993. — V.205. — P.204-ORGN.
- W. Adam, R. Curci, J.O. Edwards, Dioxiranes: a New Class of Powerful Oxidants IIAcc. Chem. Res. 1989. — V.22. — № 6. — P.205−211.
- Landolt-Bornsten, Kinetische Konstanten Von Radikalreaktionen In Flussigkeiten. Zurich, 1984.
- A. Dinoi, R. Curci, P. Carloni, E. Damiani, P. Stipa, L. Greci, On the Reaction of Aminoxyls With Dioxiranes //Eur. J. Org. Chem. 1998. — № 5. -P.871−876.
- Organische Peroxo-Verbindungen. Vol. Е13. Stuttgart, 1988.
- О. Reiser, Oxidation of Weakly Activated C-H Bonds HAngew. Chem.-Int. Edit. Engl. 1994. — V.33. — № 1. — P.69−72.
- D.S. Teager, R.K. Murray, Oxidation of 2,4-Didehydroadamantane HJ. Org. Chem. 1993. — V.58. — № 20. — P.5548−5550.
- R.W. Murray, R. Jeyaraman, L. Mohan, Chemistry of Dioxiranes .4. Oxygen Atom Insertion Into Carbon- Hydrogen Bonds by Dimethyldioxirane IIJ. Am. Chem. Soc. 1986. — V.108. — № 9. — P.2470−2472.
- R. Mello, L. Cassidei, M. Fiorentino, C. Fusco, R. Curci, Oxidations by Methyl (Trifluoromethyl)Dioxirane .2. Selective Polyoxyfunctionalization of Adamantane //Tetrahedron Lett. 1990. — V.31. — № 21. — P.3067−3070.
- C. Fusco, M. Fiorentino, A. Dinoi, R. Curci, Oxyfunctionalization of Non-Natural Targets by Dioxiranes .2. Selective Bridgehead Dihydroxylation of Fenestrindane IIJ. Org. Chem. 1996. — V.61. — № 24. — P.8681−8684.
- D. Kuck, A. Schuster, C. Fusco, M. Fiorentino, R. Curci, Oxyfunctionalization of Nonnatural Targets by Dioxiranes Selective Oxidation of Centropolyindans IIJ. Am. Chem. Soc. — 1994. — V.116. — № 6. -P.2375−2381.
- C. Cerre, A.F. Hofmann, C.D. Schteingart, W.P. Jia, D. Maltby, Oxyfunctionalization of (5 Beta)-Bile Acids by Dimethyldioxirane: Hydroxylation At C-5, C-14, and C-17 //Tetrahedron 1997. — V.53. — № 2. -P.435−446.
- B. Voigt, A. Porzel, D. Golsch, W. Adam, G. Adam, Regioselective Oxyfunctionalization of Brassinosteroids by Methyl (Trifluoromethyl)
- Dioxirane: Synthesis of 25-Hydroxy- Brassinolide and 25-Hydroxy-24-Epibrassinolide by Direct C-H Insertion /'/Tetrahedron 1996. — V.52. -№ 32. — P.10 653−10 658.
- P. Bisseret, M. Rohmer, Dimethyldioxirane Oxidation of Isomeric Triterpenes of the Hopane Series //Tetrahedron Lett. 1993. — V.34. — № 7. -P.1131−1132.
- P. Bovicelli, P. Lupattelli, V. Fiorini, E. Mincione, Oxyfunctionalization of Steroids by Dioxiranes Site and Stereoselective C)4 and C17 Hydroxylation of Pregnane and Androstane Steroids //Tetrahedron Lett. — 1993. — V.34. -№ 38. — P.6103−6104.
- M.E. Gonzalez-Nunez, J. Royo, G. Castellano, C. Andreu, C. Boix, R. Mello, G. Asensio, Hyperconjugative Control by Remote Substituents of Diastereoselectivity In the Oxygenation of Hydrocarbons //Org. Lett. 2000. — V.2. — № 6. — P.831−834.
- R. Mello, M. Fiorentino, C. Fusco, R. Curci, Oxidations by Methyl (Trifluoromethyl)Dioxirane .2. Oxyfunctionalization of Saturated-Hydrocarbons IIJ. Am. Chem. Soc. 1989. — V.lll. — № 17. — P.6749−6757.
- G.D. Maynard, L.A. Paquette, Divergent Response of a Hindered Cyclopropene to Strong Oxidizing-Agents HJ. Org. Chem. 1991. — V.56. -№ 18. — P.5480−5482.
- G. Asensio, R. Mello, M.E. Gonzaleznunez, G. Castellano, J. Corral, a General and Efficient Method for the Monohydroxylation of Alkanes HAngew. Chem.-Int. Edit. Engl. 1996. — V.35. — № 2. — P.217−218.
- R.W. Murray, M.K. Pillay, Dioxiranes Dimethyldioxirane Catalyzed Valence Isomerization of Quadricyclane //Tetrahedron Lett. — 1988. — V.29. -№ 1. — P.15−18.
- R.W. Murray, M.K. Pillay, R. Jeyaraman, Chemistry of Dioxiranes .10. Oxidation of Quadricyclane and Norbornadiene by Dimethyldioxirane HJ. Org. Chem. 1988. — V.53. — № 13. — P.3007−3011.
- R.W. Murray, H. Gu, Linear Free-Energy Relationship Studies of the Dimethyldioxirane C-H Bond Insertion Reaction HJ. Org. Chem. 1995. -V.60. -№ 17. -P.5673−5677.
- R.W. Murray, D.Q. Gu, Dioxirane Chemistry .25. the Effect of Solvent On the Dimethyldioxirane Carbon-Hydrogen Bond Insertion Reaction HJ. Chem. Soc.-Perkin Trans. 2 1994. — № 3. — P.451−453.
- F. Minisci, L.H. Zhao, F. Fontana, A. Bravo, Trapping of Free-Radicals In the Oxidation of Ethers, Aldehydes and Alkanes by Dimethyldioxirane //Tetrahedron Lett. 1995. — V.36. — № 11. — P.1895−1898.
- F. Minisci, L.H. Zhao, F. Fontana, A. Bravo, Free-Radicals In the Oxidation and Plalogenation of Alkanes by Dimethyldioxirane An Oxygen Rebound Mechanism //Tetrahedron Lett. — 1995. — V.36. — № 10. — P.1697−1700.
- R. Curci, A. Dinoi, C. Fusco, M.A. Lillo, On the Triggering of Free Radical Reactivity of Dimethyldioxirane //Tetrahedron Lett. 1996. — V.37. — № 2. -P.249−252.
- P.A. Simakov, S.Y. Choi, M. Newcomb, Dimethyldioxirane Hydroxylation of a Hypersensitive Radical Probe: Supporting Evidence for An Oxene Insertion Pathway //Tetrahedron Lett. 1998. — V.39. — № 45. — P.8187−8190.
- R. Vanni, S.J. Garden, J.T. Banks, K.U. Ingold, Mechanism of Hydroxylation of Alkanes by Dimethyldioxirane a Radical-Clock Study //Tetrahedron Lett. — 1995. — V.36. — № 44. — P.7999−8002.
- G. Asensio, R. Mello, M.E. Gonzaleznunez, C. Boix, J. Royo, the Oxidation of Alkanes With Dimethyldioxirane- a New Mechanistic Insight //Tetrahedron Lett. 1997. — V.38. — № 13. — P.2373−2376.
- A. Bravo, F. Fontana, G. Fronza, F. Minisci, L.H. Zhao, Molecule-Induced Homolysis Versus «Concerted Oxenoid Oxygen Insertion» In the Oxidation of Organic Compounds by Dimethyldioxirane HJ. Org. Chem. 1998. -V.63. -№ 2. -P.254−263.
- Д.В. Казаков, H.H. Кабальнова, С. Л. Хурсан, В. В. Шерешовец, Кинетические Закономерности Взаимодействия Диметилдиоксирана С Кумолом IIИзв. АН. Сер. Хим. 1997. — № 4. — Р.694−702.
- S.A. Grabovskiy, A.V. Antipin, N.N. Kabal’nova, the Role of Free Radicals In the Reaction of Dimethyldioxirane With Adamantane IIKinetics and Catalysis 2004. — V.45. — № 6. — P.809−812.
- S. Shaik, M. Filatov, D. Schroder, H. Schwarz, Electronic Structure Makes a Difference: Cytochrome P-450 Mediated Hydroxylations of Hydrocarbons As a Two-State Reactivity Paradigm //Chem. Eur. J. 1998. — V.4. — № 2. -P.193−199.
- M.N. Glukhovtsev, С. Сапера, R.D. Bach, the Nature of the Transition Structure for the Oxidation of Alkanes With Dioxiranes HJ. Am. Chem. Soc. 1998. — V.120. — № 40. — P. l0528−10 533.
- X. Du, K.N. Houk, Transition States for Alkane Oxidations by Dioxiranes HJ. Org. Chem. 1998. — V.63. — № 19. — P.6480−6483.
- M. Freccero, R. Gandolfi, M. Sarzi-Amade, A. Rastelli, Transition Structures for the Stepwise Insertion of Oxygen Into Alkane Tertiary C-Ii Bonds by Dimethyldioxirane //Tetrahedron Lett, 2001. — V.42. — № 14. -P.2739−2742.
- R. Curci, L. DAccolti, C. Fusco, a Novel Approach to the Efficient Oxygenation of Hydrocarbons Under Mild Conditions. Superior Oxo Transfer Selectivity Using Dioxiranes HAcc. Chem. Res. 2006. — V.39. -№ 1. — P.1−9.
- A.A. Fokin, В.А. Tkachenko, O.I. Korshunov, P.A. Gunchenko, P.R. Schreiner, Molecule-Induced Alkane Homolysis With Dioxiranes IIJ. Am. Chem. Soc. 2001. — V.123. — № 45. — P. 11 248−11 252.
- R. Mello, L. Cassidei, M. Fiorentino, C. Fusco, W. Hummer, V. Jager, R. Curci, Oxidations by Methyl (Trifluoromethyl)Dioxirane .5. Conversion of Alcohols Into Carbonyl-Compounds HJ. Am. Chem. Soc. 1991. — V.113. -№ 6. — P.2205−2208.
- R. Ballini, F. Papa, P. Bovicelli, Selective Oxidation of Nitrocompounds by Dimethyldioxirane //Tetrahedron Lett. 1996. — V.37. — № 20. — P.3507−3510.
- F. Kovac, A.L. Baumstark, Oxidation of Alpha-Methylbenzyl Alcohols by Dimethyldioxirane //Tetrahedron Lett. 1994. — V.35. — № 47. — P.8751−8754.
- M.A. Cunningham, P.C. Vasquez, P.J. Franklin, A.L. Baumstark, Oxidation of Secondary Aliphatic Alcohols by Dimethyldioxirane: Kinetics and Selectivity HHeterocycl. Commun. 1998. — V.4. — № 3. — P.201−204.
- C.A. Грабовский, E.C. Суворкина, H.H. Кабальнова, СЛ. Хурсан, B.B. Щерешовец, Окисление Спиртов Диметилдиоксираном НИзв. АН, Сер. Хим. 2000. — № 8. — Р.1338−1343.
- P. Bovicelli, P. Lupattelli, A. Sanetti, Е. Mincione, Selective Oxidation of Diols by H2o2/Ts-l System and by Dmdo //Tetrahedron Lett. 1994. -V.35. — № 45. — P.8477−8480.
- P. Bovicelli, D. Truppa, A. Sanetti, R. Bernini, P. Lupattelli, Regioselective Oxidation of Azidodiols, Bromodiols and Triol Derivatives by Dimethyldioxirane //Tetrahedron 1998. — V.54. — № 47. — P.14 301−14 314.
- R. Curci, L. Daccolti, A. Detomaso, C. Fusco, K. Takeuchi, Y. Ohga, P.E. Eaton, Y.C. Yip, Selective Oxidation of Tertiary-Secondary Vic-Diols to Alpha- Hydroxy Ketones by Dioxiranes //Tetrahedron Lett. 1993. — V.34. -№ 28. — P.4559−4562.
- P. Bovicelli, P. Lupattelli, A. Sanetti, E. Mincione, Efficient Desymmetrization of 1,2-Diol and 1,3-Diol by Dimethyldioxirane //Tetrahedron Lett. 1995. — V.36. — № 17. — P.3031−3034.
- P. Bovicelli, A. Sanetti, P. Lupattelli, Fine Regioselective Tuning In the Oxidation of Sec, Sec 1,2- Diols by Dimethyldioxirane //Tetrahedron 1996. — V.52. — № 33. — P.10 969−10 978.
- W. Adam, C.R. Saha-Moller, C.G. Zhao, Enantioselective Oxidation of Vic-Diols to Optically Active Alpha-Hydroxy Ketones by a Fructose-Derived Dioxirane //Tetrahedron: Asymmetry 1998. — V.9. — № 23. — P.4117−4122.
- W. Adam, C.R. Saha-Moller, C.G. Zhao, Asymmetric С H Oxidation of Vic-Diols to -Hydroxy Ketones by a Fructose-Derived Dioxirane: Electonic Effects On the Enantioselectivity of Oxygen Transfer IIJ. Org. Chem. -1999. V.64. — № 20. — P.7492−7497.
- R. Curci, L. Daccolti, A. Dinoi, C. Fusco, A. Rosa, Selective Oxidation of O-Isopropylidene Derivatives of Diols to 2-Hydroxy Ketones Employing Dioxiranes //Tetrahedron Lett. 1996. — V.37. — № 1. — P.115−118.
- P. Bovicelli, P. Lupattelli, D. Fracassi, E. Mincione, Sapogenins and Dimethyldioxirane a New Entry to Cholestanes Functionalized At the Side-Chain //Tetrahedron Lett. — 1994. — V.35. — № 6. — P.935−938.
- F.R.Y. Heerden, J.T. Dixon, C.W. Holzapfel, Direct Transformation of Steroidal Ethers Into Ketones by Dimethyldioxirane //Tetrahedron Lett. -1992. V.33. — № 48. — P.7399−7402.
- R. Curci, L. Daccolti, M. Fiorentino, C. Fusco, W. Adam, M.E. Gonzaleznunez, R. Mello, Oxidation of Acetals, An Orthoester, and Ethers by Dioxiranes Through Alpha-Ch Insertion //Tetrahedron Lett. 1992. -V.33. — № 29. — P.4225−4228.
- B.A. Marples, J.P. Muxworthy, K.H. Baggaley, Oxidative Cleavage of Benzyl Ethers Using Dimethyldioxirane HSynlett 1992. — № 8. — P.646.
- P. Bovicelli, A. Sanetti, R. Bernini, P. Lupattelli, Oxyfunctionalisation of Activated Methylenes by Dimethyldioxirane: An Easy Conversion of Isochromans Into Isocoumarins //Tetrahedron 1997. — V.53. — № 28. -P.9755−9760.
- M. Ferrer, F. Sanchezbaeza, J. Casas, A. Messeguer, Decomposition of Dioxiranes Induced by Dialkyl Ethers //Tetrahedron Lett. 1994. — V.35. -№ 18. — P.2981−2984.
- S.A. Grabovskiy, Q.K. Timerghazin, N.N. Kabal’nova, Oxidation of Ethers With Dimethyldioxirane HRuss. Chem. Bull. Int. Ed. 2005. — V.54. — № 10. -P.23 84—2393.
- A.L. Baumstark, F. Kovac, P.C. Vasquez, Oxidation of Secondary Alcohols and Ethers by Dimethyldioxirane //Can. J. Chem.-Rev. Can. Chim. 1999. -V.77. — № 3. — P.308−312.
- M. Ferrer, М. Gibert, F. Sanchezbaeza, A. Messeguer, Easy Availability of More Concentrated and Versatile Dimethyldioxirane Solutions //Tetrahedron Lett. 1996. — V.37. — № 20. — P.3585−3586.
- M. Gibert, M. Ferrer, F. Sanchezbaeza, A. Messeguer, Availability and Reactivity of Concentrated Dimethyldioxirane Solutions In Solvents Other Than Acetone //Tetrahedron 1997. — V.53. — № 25. — P.8643−8650.
- T. Kuwana, Photonometric Titration of Dissolved Oxygen and Cu (II) HAnalyt. Chem. 1963. — V.35. — № 10. — P.1398−1402.
- С.Д. Разумовский, Кислород элементарные формы и свойства. Москва, Химия, 1979, 304 с.
- S. Bornemann, D.H.G. Crout, Н. Dalton, V. Kren, М. Lobell, G. Dean, N. Thomson, M.M. Turner, Stereospecific Formation of R-Aromatic Acyloins by Zymomonas Mobilis Pyruvate Decarboxylase HJ. Chem. Soc., Perkin Trans. 1 1996. -P.425.
- F. Neuser, H. Zorn, R.G. Berger, Generation of Odorous Acyloins by Yeast Pyruvate Decarboxylases and Their Occurrence In Sherry and Soy Sauce HJ. Agric. Food Chem. 2000. — V.48. — P.6191−6195.
- L. Cottrell, B.T. Golding, T. Munter, W.P. Watson, In Vitro Metabolism of Chloroprene: Species Differences, Epoxide Stereochemistry and a Dechlorination Pathway И Chem. Res. Toxicol. 2001. — V.14. — P. 1552−1562.
- D.R. Boyd, D. Clarke, M.C. Cleij, J.T.G. Hamilton, G.N. Sheldrake, Bacterial Biotransformation of Isoprene and Related Dienes HMonatsh. Chem. 2000. — V. 131. — P.673−685.
- I-I. Kropf, S. Munke, In. Vol. E13. Stuttgart, Houben-Weyl, 1988, P.1395.
- M. Freccero, R. Gandolfi, M. Sarzi-Amade, A. Rastelli, Novel Pathways for Oxygen Insertion Into Unactivated C-H Bonds by Dioxiranes. Transition
- Structures for Stepwise Routes Via Radical Pairs and Comparison With the Concerted Pathway IIJ. Org. Chem. 2003. — V.68. — № 3. — P.811−823.
- G.V. Shustov, A. Rauk, Mechanism of Dioxirane Oxidation of CH Bonds: Application to Homo- and Heterosubstituted Alkanes As a Model of the Oxidation of Peptides IIJ. Org. Chem. 1998. — V.63. — № 16. — P.5413−5422.
- B.C. Gilbert, R.O.C. Norman, G. Placucci, R.C. Sealy, Electron Spin Resonance Studies. Part XLV. Reactions of the Methyl Radical With Some Aliphatic Compounds In Aqueous Solution IIJ. Chem. Soc., Perkin Trans. 2- 1975. № 9. — P.885−891.
- E.T. Денисов, Н. И. Мицкевич, B.E. Агабеков, Механизм жидкофазного окисления кислородсодержагцих соединений. Минск, Наука и техника, 1975,336 с.
- С. А. Грабовский, Н. Н. Кабальнова, В Кн. Современный органический синтез, Химия, Москва, 2003, С. 252.
- W. Adam, L.P. Hadjiarapoglou, R. Curci, R. Mello, In Organic Peroxides, 1992.
- P. Neta, R.E. Huie, A.B. Ross, Rate Constants for Reactions of Peroxyl Radicals In Fluid Solutions IIJ. Phys. Chem. Ref. Data 1990. — V.19. — № 2.- P.413−513.