Изучение синтетических возможностей нитрозирования гемдигалогенциклопропанов: синтез 5-галогенизоксазолов
Диссертация
Научная новизна и практическая значимость. Разработан препаративный метод синтеза 5-хлори 5-бромизоксазолов нитрозированием 1,1-дигалогенциклопропанов комплексом N001−2803. На примере дихлори дибромциклопропанов различного строения, содержащих алифатические и ароматические заместители в трехчленном цикле, а также дигалогенциклопропанов полициклического строения, проведено систематическое… Читать ещё >
Список литературы
- Eicher Т., Hauptmann S., Speicher A. The Chemistry of Heterocycles Structure, Reactions, Syntheses, and Applications. Weinheim: Wiley-VCH. 2003, 138.
- Baraldi P.G.- Barco A.- Benetti S.- Pollini G.P.- Simoni D. The Use of Isoxazoles as 1,3 Dicarbonyl Equivalents in Organic Synthesis. Synthesis. 1987, 857.
- Laue Т., Plagens A. Named organic Reactions. Weinheim: Wiley-VCH. 2005,317.
- Madsen U., Brauner-Osborne H., Frydenvang K., Hvene L., Johansen TN. Synthesis and Pharmacology of 3-Isoxazolol Amino Acids as Selective Antagonists at Group I Metabotropic Glutamic Acid Receptors. J. Med. Chem. 2001, 44, 1051.
- Lautens M., Roy A. Synthetic studies of the formation of oxazoles and isoxazoles from N-acetoacetyl derivatives: scope and limitations. Org.Lett. 2000, 2 (4), 555.
- Chauhan S.S., and Joshi Y.C. Solid phase synthesis of isoxazoles derivatives. Rasayan J. Chem. 2008, 1 (3), 475.
- Юровская M. А. Методы синтеза и химические свойства ароматических гетероциклических соединений (методическая разработка). М.: изд. МГУ. 2005.
- Shen D.M., Shu M., Chapman K.T. Versatile and efficient solid-phase syntheses of pyrazoles and isoxazoles. Org. Lett. 2000, 2 (18), 2789.
- Katritzky, A. R., Wang, M., Zhang, S., Voronkov, M. V. Regioselective Synthesis of Polysubstituted Pyrazoles and Isoxazoles. J. Org. Chem. 2001, 66, 6787.
- Savant M., Pansuriya M., Bhuva C., Kapuriya N., Patel A., Audichya V., Pipaliya P., and Naliapara Y. Water Mediated Construction of Trisubstituted Pyrazoles/Isoxazoles Library Using Ketene Dithioacetals. J. Comb. Chem. 2010, 72(1), 176.
- Nishiwaki N., Ogihara T., Takami T., Tamura M., Ariga M. New synthetic equivalent of nitromalonaldehyde treatable in organic media. J.Org.Chem. 2004, 69, 8382.
- Olivera R., SanMartin R., Domi’nguez E., Solans X., Urtiaga M., and Arriortua M. A Convenient Strategy for the Synthesis of 4,5-Bis (o-haloaryl)isoxazoles. J. Org. Chem. 2000, 65, 6398.
- Lee H., Yun E., Min J., Yoon K. Choung D., & Lee S. Convenient Synthesis of an Isoxazole Compound, KRIBB3, as an Anticancer Agent. Synthetic Communications. 2012, 42 (13), 1890.
- Tang S., He J., Sun Y. Efficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted Isoxazoles. Org. Lett. 2009,11 (17), 3982.
- Tang S., He J., Sun Y., He L. and She X. Efficient and Regioselective Synthesis of 5-Hydroxy-2 -isoxazolines: Versatile Synthons for Isoxazoles, P-Lactams, and y-Amino Alcohols. J. Org. Chem. 2010, 75 (6), 1961.
- Kurangi R. F., Kawthankar R., Sawal S., Desai V. G., Tilve, S. G. Convenient Synthesis of 3,5-Disubstituted Isoxazoles. Synth. Commun. 2007, 37, 585.
- Waldo J. and Larock R. Synthesis of Isoxazoles via Electrophilic Cyclization. Org. Lett. 2005, 5 (23), 5203.
- Waldo J., Larock R. Synthesis of Isoxazoles via Electrophilic Cyclization. J. Org. Chem. 2007, 72, 9643.
- Waldo J., Mehta S., Neuenswander В., Lushington G., and Larock R. Solution Phase Synthesis of a Diverse Library of Highly Substituted Isoxazoles. J. Comb. Chem. 2008, 10 (5), 658.
- Praveen C., Kalyanasundaram A., Perumal P. Т., Gold (III)-Catalyzed Synthesis of Isoxazoles by Cycloisomerization of a, f3-Acetylenic Oximes. Synlett. 2010, 777.
- Ueda M., Sato A., Ikeda Y., Miyoshi T. Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers. Org. Lett. 2012, 12 (11), 2594.
- Ueda M., Sugita S., Sato A., Miyoshi Т., and Okiko Miyata. Copper-Catalyzed Synthesis of Trisubstituted Isoxazoles via a Cascade Cyclization-Migration Process. J. Org. Chem. 2012, 77 (20), 9344.
- She Zh., Niu D., Chen L., Gunawan M., Shanja X., Hersh W., and Chen Y. Synthesis of Trisubstituted Isoxazoles by Palladium (II)-Catalyzed Cascade Cyclization-Alkenylation of 2-Alkyn-l-one O-Methyl Oximes. J. Org. Chem. 2012, 77 (7), 3627.
- Gayon E., Quinonero O., Lemouzy S., Vrancken E., Campagne J.-M., Transition-metal-catalyzed uninterrupted four-step sequence to access trisubstituted isoxazoles. Org. Lett. 2011, 13 (24), 6418.
- Murarka S., and Studer A. Zinc Triflate Catalyzed Aerobic Cross: Dehydrogenative Coupling (CDC) of Alkynes with Nitrones: A New Entry to Isoxazoles. Org. Lett. 2011, 13 (10), 2746.
- Wang L., Yu X., Feng X., and Bao M. Synthesis of 3,5-Disubstituted Isoxazoles via Cope-Type Hydroamination of 1,3-Dialkynes. Org. Lett. 2012, 14 (9), 2418.
- Trogu E., De Sarlo F., Cardini G., Machetti F. Synthesis of Isoxazole Derivatives by
- Catalytic Condensation of Primary Nitro Compounds with Dipolarophiles. 20 072 009 (обзор).
- Kim J. and Ryu E. A Convenient Synthesis of Benzohydroximoyl Chlorides as Nitrile Oxide Precursors by HCl/N, N-Dimethylformamide/Oxone System. J. Org. Chem. 1992, 57, 6649.
- Moriya O., Urata Y., Endo T. Dehydrochlorination of Hydroximic Acid Chlorides by the Use of Organotin Compounds: An Application for Synthesis of lsoxazolines and lsoxazoles. J. Chem. Soc., Chem. Commun. 1991, 17.
- Liu K.-C. et al. A Particularly Convenient Preparation of Benzohydroximinoyl Chlorides (Nitrile Oxide Precursors). J. Org. Chem. 1980, 45 (19), 3916.
- Singh B. et al. Iodobenzene Dichloride An Efficient Reagent for Preparation of NitrileOxides from Aldoximes. Synth. Comm. 1991, 27, 1625.
- Jawalekar A., Reubsaet E., Rutjes F. T. and Delft F. Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes. Chem. Commun. 2011, 47, 3198.
- Sanders В., Friscourt F., Ledin P., Mbua N., Arumugam S., Guo J., Boltje Th., Popik V., and Boons G. Metal-Free Sequential 3 + 2.-Dipolar Cycloadditions using Cyclooctynes and 1,3-Dipoles of Different Reactivity. J. Am. Chem. Soc. 2011, 133 (4), 949.
- Moriya O. et al. Synthesis of isoxazolines and isoxazoles from aldoximes by the use of sodium bromite with organotin halide. Tet. Lett. 1989, 30, 3987.
- Mukaiyama T. and Hoshino T. The reactions of primary nitro paraffins with isocyanates J. Am. Chem. Soc. 1960, 82, 5339.
- Wankhede K., Vaidya V., Sarang P., Salunkhe M., Trivedi G. Synthesis of novel isoxazole-linked steroidal glycoconjugates—an application of a novel steroidal nitrile oxide. Tetrahedron Letters. 2008, 49, 2069.
- Weimin P., Shizheng Z. Convenient synthesis of 5-perfluoroalkylsubstituted isoxazoles. Tetrahedron. 2001, 57(27), 5781.
- Shimizu T. et al. Bull. Chem. Soc. Japan. 1986, 59, 2827.108
- Cecchi L., De Sarlo F., Machetti F., l, 4-Diazabicyclo2.2.2.octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the Base. Eur. J. Org. Chem. 2006, 4852.
- Демина O.B., Вржещ П. В., Ходонов А. А., Козловский В. И., Варфоломеев С. Д. Синтез новых ингибиторов агрегации тромбоцитов -замещенных пиридилизоксазолов и их 4,5 дигидроаналогов. Биоорганическая Химия. 1995, 21 (12), 933.
- Itoh К., Takahashi S., Ueki Т., Sugiyama Т.,. Takahashi Т. Т, Horiuchi С.А. A novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives using ammonium cerium nitrate (CAN). Tetrahedron Lett. 2002, 43,1035.
- Itoh K. Horiuchi C.A. Formation of isoxazole derivatives via nitrile oxide using ammonium cerium nitrate (CAN): a novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives. Tetrahedron. 2004, 60, 1671.
- Itoh K., Sakamaki H., Nakazato N., Horiuchi A., Horn E., Horiuchi A. A convenient and efficient one-pot synthesis of 3-acylisoxazoles using iron (III) salts. Synthesis. 2005, 3541.
- Yuan Q., Liu Z., Xiong Ch., Wu L. A novel, broad-spectrum antitumor compound containingthe l-hydroxycyclohexa-2,5-dien-4-one group: The disclosure of a new antitumor pharmacophore in protoapigenone 1. Bioorg. & Med. Chem. Lett. 2011, 21, 3427.
- Himo F., Lovell Т., Hilgraf R. Copper (I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates. J. Am. Chem. Soc. 2005, 727, 210.
- Hansen Т., Wu P., and Fokin V. One-Pot Copper (I)-Catalyzed Synthesis of 3,5-Disubstituted Isoxazoles. J. Org. Chem. 2005, 70 (19), 7761.
- Vieira A., Bryk F., Conte G., Bortoluzzi A., Gallardo H. 1,3-Dipolar cycloaddition reaction applied to synthesis of new unsymmetric liquid crystal compounds-based isoxazole. Tetrahedron Letters. 2009, 50, 905.
- Jackowski O., Lecourt T., Micouin L., Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization. Org. Lett. 2011,13, 5664.
- Willy B., Rominger F., Miiller T. J. J. Novel Microwave-Assisted One-Pot Synthesis of Isoxazoles by a Three-Component Coupling-Cycloaddition Sequence. Synthesis. 2008, 293.
- Hashimoto Y., Takada A., Takikawa H. and Suzuki K. Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts. Org. Biomol. Chem. 2012, 10, 6003.
- Venkata Ramana P. and Reddy R. A. Synthesis of 1,2,3-Triazole Substituted Isoxazoles via Copper (I) Catalyzed Cycloaddition. J. Heterocyclic Chem. 2012, 49, 621.
- Barrett A.G.M., Procopiou P.A., Voigtmann U. Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches. Org. Lett. 2001, 3 (20), 3165.
- Bode J., Hachisu Y., Matsuura T., and Suzuki K. Facile Construction and Divergent Transformation of Poly cyclic Isoxazoles: Direct Access to Polyketide Architectures. Org. Lett. 2003, 5 (4), 391.
- Lee Ch. Ch., Fitzmaurice R. and Caddick S. 3,5-Isoxazoles from a-bromo-pentafluorophenyl vinylsulfonates: Synthesis of sulfonates and sulfonamides. Org. Biomol. Chem. 2009, 7, 4349.
- Xu J., Hamme II A. T. Efficient Access to Isoxazoles from Alkenes. Synlett. 2008, 919.
- Sheng S.-R., Liu X.-L., Xu Q., Song C.-S., One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide. Synthesis. 2003, 2763.
- Bourbeau M. and Rider J. A Convenient Synthesis of 4-Alkyl-5-aminoisoxazoles. Org. Lett. 2006, 8 (17), 3679.
- Koranne P., Tsujihara T., Arai M. Design and synthesis of chiral hybrid spiro (isoxazole-isoxazoline) ligands. Tetrahedron: Asymmetry. 2007,18, 919.
- Dubrovskiy A. and Larock R. Synthesis of Benzisoxazoles by the 3+2. Cycloaddition of in situ Generated Nitrile Oxides and Arynes. Org. Lett. 2010, 12 (6), 1180.
- Kantorowski E.J., Kurth M.J. Solid-phase synthesis of isoxazoles and isoxazolines: en route toa new class of ionophores. J. Org. Chem. 1997, 62, 6797.
- Barrett A.G.M., Procopiou P.A., Voigtmann U. Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches. Org. Lett. 2001, 3 (20), 3165.
- Tanaka M., Haino T., Ideta K., Kubo K., Morib A. Fukazawa Y. Combinatorial synthesis of isoxazole library and their liquid crystalline properties. Tetrahedron. 2007, 63, 652.
- Lee Y., Koyama Y., Yonekawa M. and Takata T. New Click Chemistry: Polymerization Based on 1,3-Dipolar Cycloaddition of a Homo Ditopic Nitrile NOxide and Transformation of the Resulting Polymers into Reactive Polymers.
- Macromolecules. 2009, 42 (20), 7709.
- Cecchi L., Sarlo F., Machetti F. l, 4-Diazabicyclo2.2.2.octane (DABCO) as an Efficient Reagent for the Synthesis of Isoxazole Derivatives from Primary Nitro Compounds and Dipolarophiles: The Role of the Base. Eur. J. Org. Chem. 2006, 27,4852.
- Easton Ch. J., Hughes C. M. and Tiekink E. R. Reversal of Regiochemlstry in the Synthesis of Isoxazoles by Nitrile Oxide Cycloadditions. Tetrahedron Lett. 1994, 35, 3589.
- Raihan M. J., Kavala V., Habib P. M. Synthesis of Isoxazoline N-Oxides via Hydroxy (tosyloxy)iodo.benzene (HTIB)-Mediated Oxidative N-0 Coupling. J. Org. Chem. 2011, 76, 424.
- Zhong С., Gautam L. N. S., Petersen J. L., Akhmedov N. G., Shi X. Concise Asymmetric Synthesis of Fully Substituted Isoxazoline-N-oxide Through Lewis Base Catalyzed Nitroalkene Activation. Chem. Eur. J. 2010, 16, 8605.
- Chemagin A. V., Yashin N. V., Grishin Y. K., Kuznetsova T. S., Zefirov N. S. Diethyl Nitro (diazo)methyl.phosphonate: Synthesis and Reactivity towards Alkenes. Synthesis. 2010, 259.
- Dieter R. K. and Chang H. J. Synthesis of Isoxazoles and Isothiazoles from a-Oxo-Ketene Dithioacetals. J. Org. Chem. 1989. 54, 1088.
- Barber G. N. and Olofson R. A. A Useful, Regiospecific Synthesis of Isoxazoles. J. Org. Chem. 1978, 43, 3015.
- Mohamed Ahmed M. S., Kobayashi K., and Mori A. One-Pot Construction of Pyrazoles and Isoxazoles with Palladium-Catalyzed Four-Component Coupling. Org. Lett. 2005, 7 (20), 4487.
- Stokes B. J., Vogel С. V., Urnezis L. K., Pan M., and Driver T. G. Intramolecular Fe (II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides. Org Lett. 2010, 12 (12), 2884.
- Сычкова JT. Д. Шабаров Ю. С. Взаимодействие 1,2-диарилциклопропаиов с нитратов меди в укусусном ангидриде как метод синтеза 3,5-диарилизоксазолов. ЖОрХ. 1985, 21, 292.
- Сагинова JI. Г, Мохаммад Альхамдан, Петросян В. С. гем-Дигалогенциклопропаны в реакциях нитрозирования с нитратом натрия в трифторуксусной и серной кислотах. Вест. Моск. Универ. Сер.2. Химия. 1998, 39, 339.
- Lin Sh., Kuo Sh., Yang F. Reaction of Halogenated Cyclopropanes and Nitrosyl Cation: Preparation of Isoxazoles. J. Org. Chem. 1997, 62, 5229.
- Зык H. В., Бондаренко О. Б., Гаврилова А. Ю., Чижов А. О., Зефиров Н. С. гем-Дихлоралкилциклопропаны в реакции с NOCl*2 SO3: синтез алкилзамещенных 5-хлоризоксазолов. Изв. АН. Сер. хим. 2011. 2. 321.
- Li G., Kakarla R. and Gerritz S. W. A fast and efficient bromination of isoxazoles and pyrazoles by microwave irradiation. Tetrahedron Lett. 2007, 48, 4595.
- Schnurch M., Flasik R., Khan A. F., Spina M., Mihovilovic M. D., Stanetty P. Cross-Coupling Reactions on Azoles with Two and More Heteroatoms. Eur. J. Org. Chem. 2006, 3283.
- Huang X., Shipps G. W., Cheng Jr. C., Spacciapoli P. Discovery and Hit-to-Lead Optimization of Non-ATP Competitive MK2 (MAPKAPK2) Inhibitors. ACS
- Med. Chem. Lett. 2011, 2, 632.
- Ratcliffe P., Abernethy L., Ansari N., Cameron K., Clarkson Т., Dempster M. Discovery of potent, soluble and orally active TRPV1 antagonists. Structure-activity relationships of a series of isoxazoles. Bioorg. Med. Chem. Lett. 2001, 21, 4652.
- Crossley J. A. and Browne D. L. An Alkynyliodide Cycloaddition Strategy for the Construction of Iodoisoxazoles. J. Org. Chem. 2010, 75, 5414.
- Ku Y., Grieme Т., Sharma P., Pu Y., Raje P. Use of Iodoacetylene as a Dipolarphile in the Synthesis of 5-Iodoisoxazole Derivatives. Org. Lett. 2001, 3 (26), 4185.
- Stevens R.V. and Albizati K.F. Synthesis and Nucleophilic Substitutions of 3-alkyl-5chloroisoxazoles. Tetrahedron Letters. 1984, 25, 4587.
- Takenaka K., Nakatsuka Sh., Tsujihara Т., Koranne P. S., Sasai H. Divergent synthesis of chiral spiro (isoxazole-isoxazoline) hybrid ligands. Tetrahedron: Asymmetry. 2008, 19, 2492.
- Grob J. E., Nunez J., Dechantsreiter M. A., and Hamann L. G. Regioselective Synthesis and Slow-Release Suzuki-Miyaura Cross-Coupling of МГОА Boronate-Functionalized Isoxazoles and Triazoles. J. Org. Chem. 2011, 76, 10 241.
- Moore J. E., Davies M. W., Goodenough К. M. Investigation of the scope of a 3+2. cycloaddition approach to isoxazole boronic esters. Tetrahedron. 2005, 61, 6707.
- Vinick F. J., Pan Y., Gschwend H W. Preparation and reactivity of acetoacetonitrile dianion. Tetrahedron Lett. 1978,19, 4221.
- Schollkopt U., Hoppe I. a-Metalated Isocyanides in Organic Synthesis. Angew. Chem. Int. Ed. 1975, 14, 785.
- Sakamoto Т., Kondo Y., Uchiyama D., Yamanaka H. Condensed Heteroaromatic Systems. XIX. Synthesis and Reactions of 5-(tributylstannyl)isoxazoles. Tetrahedron. 1991, 47, 5111.
- Kondo Y., Uchiyama D., Sakamoto Т., Yamanaka H. Synthesis and Reactions of 5-(tributylstannyl)isoxazoles. 1989, 30, 4249.
- Iglesias M., Schuster O., Albrecht M. A new, mild one-pot synthesis of iodinated heterocycles as suitable precursors for N-heterocyclic carbene complexes. Tetrahedron Lett. 2010, 51, 5423.
- Stephens Ch. E., Blake J. A. Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor. J. Fluor. Chem. 2004,125, 1939.
- Palin R., Abernethy L., Ansari N., Cameron K., Clarkson T. Structure-activity studies of a novel series of isoxazole-3-carboxamide derivatives as TRPV1 antagonists. Bioorg. &Med. Chem. Lett. 2011, 21, 892.
- Loren Kenneth Gibbons, Medina. Arylisoxazoles as Nematicides. US Patent, 1973,3,781,438. Dec, 25.
- Yevich J. P., New J. S., Smith D. W. Synthesis and Biological Evaluation of l-(l, 2-Benzisothiazol-3-yl) — and (l, 2-Benzisoxazol-3-yl)piperazine Derivatives as Potential Antipsychotic Agents. J. Med. Chem. 1986, 29, 359.
- Griesbeck A. G., Franke M., Neudorfl J., and Kotaka H. Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies. BeilsteinJ. Org. Chem. 2011, 7, 127.
- Nantermet Ph. G., Barrow J. C., Lundell G. F. Discovery of a Nonpeptidic Small Molecule Antagonist of the Human Platelet Thrombin Receptor (PAR-1). Bioorg. & Med. Chem. Lett. 2002, 12, 319.
- Бондаренко О. Б., Сагинова JI. Г., Шабаров Ю. С. Поведение некоторыхарилциклопропанов в диоксиде серы. ЖОрХ. 1987, 23, 1114.114
- Шабаров Ю. С., Сагинова JI. Г., Газзаева Р. А. Синтез изоксазолинов из арилциклопропанов в условиях нитрозирования. Х.Г.С. 1983. 738.
- Газзаева Р. А., Шабаров Ю. С., Сагинова JI. Г. Замещенные фенициклопропаны в синтезе 2-изоксазолинов. Х.Г.С. 1984, 309.
- Mizuno К., Ichinose N., Tamai Т., Otsuji Y. Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies. J. Org. Chem. 1992, 57, 4669.
- Бондаренко О. Б., Гаврилова А. Ю., Сагинова JI. Г., Зык Н. В., Зефиров Н. С. Дг-Изоксазолины из арилциклопропанов: реакция с нитрозилхлоридом, активированным триоксидом серы. Изв. АН. Сер. хим. 2003, 741.
- Грандберг К. И., Кабачник М. М., Сагинова JI. Г., Теренин В. И. Практические работы по органической химии (Методическое пособие). М.: изд. МГУ. 2001, 3(14), 37.
- Костиков P.P., Молчанов А. П., Беспалов А. Я. Реакции карбенов с сопряженными ди- и полиеновыми соединениями. Реакция дихлоркарбена с 2-фенил-1,3-бутадиеном. ЖОХ. 1974, 10, 10.
- Зефиров Н. С., Казимирчик И. В., Лукин К. Л. Циклоприсоединение дихлоркарбена к олефинам. М. Наука. 1985, 152.
- Арбузова Т., В., Хамидуллина А. Р., Злотский С. С. Синтезы на основе винил-гем.-дихлорциклопропанов. Изв. вузов. Химия и хим. технология. 2007, 50 (6), 15.
- Хамидуллина А. Р., Брусенцова Е., А., Злотский С. С. Алкилирование бензола и толуола винил-гем.-дихлорциклопропанами. Изв. вузов. Химия и хим. технология. 2008, 51 (9), 106.
- Клеттер Е. А., Козырева Ю. П., Кутуков Д. И., Злотский С. С. Алкилирование фенолов алкенил-гем-дихлорциклопропанами. Нефтехгшия. 2010, 50 (1), 66
- Брусенцова Е., А., Колесоа С. В., Воробьева А. И., Злотский С. С., Хамидуллина А. Р., Муслухов Р. Р, Спирхин Л. В., Заиков Г. Е. Винил-гемдихлорциклопропаны в реакциях радикальной полимеризации. ЖОХ. 2008, 78 (140), 783.
- Альхамдан М., Сагинова Л.Г, Петросян B.C. Реакция гем-дихлорфенилциклопропана с нитритом натрия в трифторуксусной кислоте. Вести. МГУ, Сер. химия. 1994, 35, 357.
- Mizuno К., Ichinose N., Tamai Т., Otsuji Y. Formation of 2-Substituted 2-Isoxazolinium Salts by the Reaction of 1,1,2,2-Tetrasubstituted Cyclopropanes withNOBF4. С hem. Lett. 1989, 457.
- LaLonde R.T., Forney L.S. Carbon-Carbon Bond Fission in Cyclopropanes. I. The Acid-Promoted Opening of the Three-Membered Ring in Bicyclo 4.1.0.heptane, Bicyclo [3.1.0]hexane, and Bicyclo [2.1.0]pentane. J. Am. Chem. Soc. 196,.85, 3767.
- Сагинова JI. Г., Альхамдан М., Петросян B.C. Реакция гем-дигадогенфенилциклопропанов с нитритом натрия в концентрированной серной кислоте. Вестн. МГУ, Сер. химия. 1997, 38, 354.
- Bondarenko О.В., Gavrilova A.Yu., Polunina V.V., Starikova Z.A., Zyk N.V., Zefirov N.S. Unexpected mode of reactivity in nitrosation of cis-1,1-dichloro-2,3-diphenylcyclopropane with NOCI2SO3. Mendeleev Commun., 2009, 19, 12.
- Lin S.T., Lin L.N., Yao Y.F. Nitration of l, l-dihalo-2-(4'-nitrophenyl) cyclopropanes: New method to prepare isoxazole. Tetrahedron Lett. 1992, 33, 3155.
- Новокрещенных В.Д., Мочалов С. С., Лукашова Е. А., Шабаров Ю. С. Превращения арилзамещенных моно- и диметоксициклопропанов под действием нитрующих агентов ЖОрХ. 1984, 20, 108.
- Bandlish В.К., Shine H.J. Ion radicals. 37. Preparation and isolation of cation radical tetrafluoroborates by the use of nitrosonium tetrafluoroborate. J. Org. Chem. 1977, 42, 561.
- Mizuno K., Ichinose N., Tamai Т., Otsuji Y. Insertion of nitrogen oxide andnitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its116mechanistic studies. J. Org. Chem. 1992, 57, 4669.
- Kim E.K., Kochi J.K. Charge-transfer structures of aromatic electron donor-acceptor complexes leading to electron transfer with the electrophilic nitrosonium cation. J. Am. Chem. Soc. 1991, 113, 4962.
- Hajek M., Silhavy P., Patent Ceskoslovenska akademie ved, no. 4 806 681, 1989.
- Бондаренко О.Б., Гаврилова А. Ю., Сагинова Л. Г., Зык Н.В., Зефиров Н. С. А -Изоксазолииы из арилциклопропаиов. III. Замещенные в трехчленном цикле фенилциклопропаны в реакции с нитрозилхлоридом, активированным оксидами серы (1У, VI). ЖОрХ. 2009, 45, 230.
- Актаев Н.П., Пашинин В. А., Сокольский Г. А. Реакции а-гидротетрафторпропионитрила с электрофильными реагентами. ЖОрХ. 1974, 10, 1428.
- Бондаренко О.Б., Гаврилова А. Ю., Сагинова Л. Г., Зык Н.В. Тез. докл. Всероссийской конференции по органической химии (посвящается 75-летию со дня основания ИОХим. Н. Д. Зелинского РАН), Москва. 2009. 108
- Троянкер В. Л., Беэр А. А., Кацобашвили В. Я. Определение констант скорости реакций присоединения четыреххлористого углерода к виниловым соединениям. ЖОрХ. 1976,12, 1872.
- Bier Т., Hauthal H.G., Pritzkow W. Uber der Kinetik der NOCl-Addition an Olefine. J. Prakt. Chem. 1964. 26. 304.
- Неорганическая химия в 3 т (Под ред. Ю. Д. Третьякова). М.: Изд. центр «Академия». 2007,. 3 (2), 400.
- Гордон А., Форд Р. Спутник химика. М.: Химия. 1976, 543 с.
- Belyakov P. A., Kadentsev V. I., Chizhov А. О., Kolotyrkina N. G., Shashkov A. S., Ananikov V. P. Mechanistic insight into organic and catalytic reactions by joint studies using mass spectrometry and NMR spectroscopy. Mendeleev Commun., 2010, 20, 125.
- Нефедов О. M., Шафран Р. Н. Арил-гем-дихлорциклопропаны вреакциях электрофильного ароматического замещение. ЖОрХ., 1974,10, All.117
- Зломанов В.П. Практикум по неорганической химии. М.: изд. МГУ. 1994, 124.