Özellikle Reformatsky reaktifinin aminasyonu (i) için çok fazla uğraşılmış fakat aminasyon sağlanamadığı gibi aminasyon reaktifinin de reaksiyona girmediği gözlenmiştir. Çok az miktarda oluşan yan ürünlerin yapısı da aydınlatılamamıştır.
(ii) Arilmagnezyum ve çinko reaktiflerinin aseton O-(mesitilensülfonil)oksim ile reaksiyonunun mekanizması için fenil ve sübstitüe fenilmagnezyum bromür ve katalitik klorçinko fenil ve sübstitüe fenilsiyanokuprat bileşiklerinin aminasyonu yarışmalı kinetik yöntemle çalışılmıştır (7.3).
R1MgBr R2MgBr Me2C=NOX THF, g.s.
9 4b
Me2C=NR1 Me2C=NR2 27
H2O
R1NH2+ R2NH2 + +
+
Me2C=NOX 4b
Me2C=NR1 Me2C=NR2 27
H2O
R1NH2 + R2NH2
+ + +
R1ZnCl R2ZnCl
% 20mmol CuCN THF, o.s.
10
R1 : C6H5 a X : SO2Mes
R2 : 4-MeC6H4 b, 4-MeOC6H4 c, 4-BrC6H4 d,3-MeC6H4 e, 3-MeOC6H4 f, 3-BrC6H4 g Bu amaçla eşdeğer miktarda fakat aminasyon reaktifine göre aşırı miktarda standart fenilmetal ve sübstitüe fenilmetal karışımı aminasyon reaktifi ile reaksiyona sokulmuş ve belli sürelerde ürün aminlerin miktarları ölçülerek bağıl hız sabitleri, k2/k1 değerleri hesaplanmıştır. Arilçinko klorürlerin reaksiyonlarında katalitik olarak oluşan klorçinko arilsiyano kupratlar R1Cu(CN)ZnCl ve R2Cu(CN)ZnCl ve arilmagnezyum bromürler reaksiyonlarında karbanyonlar nükleofil olarak davranırlar. k2/k1 değerleri ile elde edilen Hammett bağıntılarının negatif eğimli doğrular olması, aminasyon reaksiyonlarının arilmagnezyum reaktiflerinde SN2 ve klorçinko arilsiyano kuprat reaktiflerinde yükseltgen katılma-indirgen ayrılma ile yürüdüğü ve reaksiyonun arilmetale ve aminasyon reaktifine göre 1. dereceden olduğu mekanizmasını (7.3a)
(7.3b)
8. KAYNAKLAR Ainsworth, C. , Chen, F. , Kuo, Y. Ketene alkyltrialkylsilyl acetals: Synthesis, pyrolysis
and NMR studies. J. Organometal. Chem. , 46 ; 59-71.
Alvernhe, G. , Laurent, A. 1978. Synthèse d’aziridines secondaires par la rèaction de Hoch-Campbell : mècanisme et limitations. J. Chem. Res. ;501.
Alvernhe, G. ,Arseniyadis, S. ,Chaabouni, R. ,Laurent, A. 1975. Synthèse d’aziridines.
Tetrahedron Letts. , 6 ; 355-356.
Alvernhe, G. ,Laurent, A. 1970. Synthèse d’aziridines par action d’organo-magnèsiens sur des oximes : Stéréochimie de la reaction. Bull.Soc.Chim.Fr. ,8-9;3003-3010.
Alvernhe, G., Laurent, A. 1972. Obtention d’amines primaires par action d’organo- magnésiens sur l’acetoxime. Tetrahedron Letts., 11; 1007-1010.
Arseniyadis, S. , Laurent, A. , Mison, A. 1980. Synthèse d’aziridines:Action d’organomagnesiens sur des iodures de N,N,N, - Trimèthylhydrazonium.
Bull. Soc. Chim. Fr. ,5-6 ; 246-254.
Askani, R. , Taber, D.F. 1996. Comprehensive organic synthesis. Trost, B.M. , Ed.;
Pergamon Press. Vol. 7; 1881 s., Oxford.
Ay, M. 1989. Doktora Tezi. A.Ü. Fen Fakültesi, 92 s. ,Ankara.
Barbero, M. , Degani, I. , Dughera, S. Fochi, R. , Perracino, P. 1998. Preparation of
diazenes by electrophilic C-coupling reactions of dry arenediazonium O-benzenedisülfonimides with Grignard reagents. Synthesis; 1235-1237.
Barbero, M., Crisma, M., Degani, I., Fochi, R., Perracino, P. 1998. New dry arenediazonium salts, stabilized to an exceptionally high degree by the anion of O- benzenedisulfonimide. Synthesis; 1171-1175.
Bartnik, R. , Laurent, A. 1974. Synthese d’aziridinecarbinols : Induction asymetrique.
Tetrahedron Letts. , 44 ; 3869-3870.
Bartnik, R. , Laurent, A. 1975. Action des rectifs de Grignard sur les oximes : Formation regiospecifiquede vinyl nitrene ; formation stereoselective d’aziridines. Bull. Soc. Chim. Fr. , 1-2 ;173-177.
Bartnik, R. ,Laurent, A. , Normant, H.M. 1974. Formation stereoselective d’aziridines a partnir d’oximes.Evidence d’un intermediaire nitrene. Compt. Rend. Acad. Sc.
Paris , Serie C , 279 ; 289-290.
Beak, P. , Basha, A. , Kakko, B. 1984. Mechanism of amination of organolithiums by alkoxyamines:Use of a geometrical test for displacement on heteroatoms.
Beak, P. , Kokko, B.J. 1982. A modification of the Schverdina-Kotscheshkow amination: The use of methoxyamine-mehyllithium as a synthetic exuivalent for NH2+. J. Org. Chem.,47; 2822-2823.
Beak, P. , Selling, G.W. 1989. Displacements at the nitrogen of lithioalkoxylamides by organometallic reagents. J.Org.Chem. , 54 ; 5574-5580.
Bertz, S. H. , Chopra, A. , Eriksson, M. , Ogle, C.A. , Seagle, P. 1999. Re-evaluation of organocuprate reactivity : Logarithmic reactivity profiles for iodo- versus cyano-Gilman reagents in the rections of organocuprates with 2-cyclohexenone and iodocyclohexane. Chem.Eur.J. , 5 ; 2680-2691.
Berzt, S. H. , Miao, G. , Eriksson, M. 1996. It’s on lithium! An answer to the recent communication which asked the question : If the cyano ligand is not on copper, then where is it ? Chem. Comm. ; 815-816.
Boche, G. , Bernheim, M. , Niedner, M. 1983. 1-Alkenylamines by electrophilic amination. Angew. Chem. Int.Ed.Engl. ,22;53-54.
Boche, G., Mayer, N., Bernheim, M., Wagner, K. 1978. Electrophilic amination of
“carbanions” with N,N-dialkyl O-aryl sulphonylhydroxylamines. Angew.
Chem. Int. Ed. Engl., 17(9); 687-688.
Boche,G. 1995. Electrophilic amination. Houben-Weyl, Methoden der Organischen Chemie. , Heimchen, G. , Hofman, R.W. , Mulzer, J. , Schaumann, E. , Eds., Vol. E 21 e; s. 5133-5157, Thieme: Stuttgart.
Braun, M. , Vanderhagen, A. , Waldmüller, D. 1995. Enantioselective Reformatsky reaction of methyl bromodifluoroacetate. Liebig. Ann. ; 1447-1450.
Brown, H.C. 1975. Laboratory operations with air-sensitive substances survey in
Campbell, K .N. , McKenna, J. F. 1939. The action of Grignard reagents on oximes. I.
The action of phenylmagnesiums bromide on mixed ketoximes. J. Org.
Chem., 4 ; 198-205.
Campbell, K.N. , Cambell, B.K. , Chaput, E.P. 1943. The reaction of Grignard reagents with oximes. II. The action of aryl Grignard reagents with mixed ketoximes.
J. Org. Chem. , 8 ; 99-102.
Campbell, K.N. , Campbell, B.K. , Hess, L.G. , Schaffner,I.J. 1944. The action of Grirnard reagents on oximes.IV. Aliphatic Grignard reagents and mixed ketoximes. J. Org. Chem. , 9;184-186.
Campbell, K.N. , Campbell, B.K. , McKenna, J.F. , Chaput, E.P. 1943. The action of Grignard reagents on oximes. III. The mechanism of the action of arylmagnesium halides on mixed ketoximes. A new synthesis of ethyleneimines.
J. Org. Chem. , 8 ; 103-109.
Carpiono, L.A. 1960. O-Acylhydroxylamines. II. O-Mesitylenesulfonyl- , O-p-toluensulfonyl- and O-mesitoylhydroxylamine. J. Am. Chem. Soc. ,82 ; 3133-3135.
Casarini, A., Dembech, P., Lazzari, D., Marini, E., Reginato, G. Ricci, A., Seconi, G.
1983. Electrophilic amination of higher order cuprates with N,O- bis(trimethylsilyl) hydroxylamine. J. Org. Chem., 58; 5620-5623.
Chaabouni, R. , Laurent, A. , Mison, P. 1973. Formation d’aziridines cyclaniques par action de reactifs de Grignard sur les oximes :Determination des configurations relatives. Tetrahedron Letts. , 12 ; 1343-1346.
Chaabouni, R. , Laurent, A. 1973. Synthèse d’aziridines par action de composès organo-mètalliques sur des oximes cyclohexaniques; ètudes des configurations relatives et des conformations. Bull. Soc. Chim. Fr. , 9-10 ; 2680-2685.
Chaabouni, R. ,Laurent, A. ,Mison, P. 1973. Formation d’aziridines cyclaniques par action de reactifs de Grignard sur les oximes; Determination des configurations relatives. Tetrahedron Letts. , 16; 1343-1346.
Clarke, H. T. , Babcock, G. S. , Murroy, T. F. 1941. Benzenesulfonyl chloride.
Closs, G .L. ,Boris, S .J. 1960. A new synthesis of aziridines. J. Am .Chem. Soc. , 82 ; 6068-6070
Coleman, G.H. , Hermanson, J.L. , Johnson, H.L. 1937. Monochloroamine with organolithium and zinc compounds. J. Am. Chem. Soc., 59; 1896-1897.
Collman, J. P. , Hegedus, L. S. 1987. Principle and applications of oragnotransition metal chemistry. University Science Books : Mill Valey , California.
Daşkapan, T.1999. Doktora Tezi. A.Ü. Fen Fakültesi, 91 s. ,Ankara.
Dembech, A. , Seconi, G. , Ricci, A. 2000. The electrophilic amination of carbanions : An unconventional new entry to C-N bond formation. Chem. Eur. J. , 6 , no:8 ; 1281-1286.
Doris, E. , Brielles, C. , Harnett, J. J. 2001. Diethylzinc / CuII – mediated alkylation of aromatic amines and related compounds. Tetrahedron Lett. , 43 ; 8301-8302.
Dubois, J. E. , Fellous, R. 1963. Synthèse de β-hydroxyesters à I’aide du complexe magnèsien de I’acètate de tertiobutyl. Bull. Soc. Chim. France ; 786-797.
Dubois, J. E. , Molnarfi, S. 1963. Sur I’existence d’un complexe magnèsien de I’acètate de tertiobutyl stable dans des milieux d’hydrocarbures. Bull. Soc. Chim. France
; 779-785.
Eguchi, S. , Ishii, Y. 1963. The mechanism and ethyleneimine formation by action of Grignard reagents on ketoximes. Chem. Soc. Bull. Jpn. , 36(11) ; 1434-1437.
Erdik, E. 1995. Organozinc Reagents in Organic Synthesis. CRC Press , 411 sayfa, New York
Erdik, E. , Ay, M. 1989. Effect of copper (I) iodide and magnesium chloride on amination of aryl Grignards with ketoximes. Synth. React. Inorg. Met.Org.
Chem., 19(7); 663-668.
Erdik, E. , Ay,M. 1989. Electrophilic amination of carbanion. Chem. Rev., 89;1947-1980
Erdik, E. , Daşkapan, T. 1999. Electrophilic amination of diarylzincs and triarylzincates
with acetone O-(2,4,6-trimethylphenylsulfonyl) oxime and with
Erdik, E. , Daşkapan, T. 1999. Electrophilic amination of organozinc reagents with acetone O-(2,4,6-trimethylphenylsulfonyl)oxime and O-methylhydroxyl- amine. J. Chem. Soc. Perkin Trans. 1; 3139-3142
Erdik, E. , Daşkapan, T. 1999. Yayınlanmamış bulgular.
Erdik, E. 1977. 1,3-Dienlerin keton hidrazonlardan türeyen vinil bakır (I) ve gümüş (I) reaktiflerinin ısıyla bozunması ile sentezi. Doçentlik Tezi, A.Ü.Fen Fakültesi, Ankara, s. 50, 56, 61.
Erdik, E. 1995. Encyclopedia of Reagents for Organic Synthesis. Paquette, L.A. Ed.;
Vol. 1 ; s.41, Wiley : New York.
Erdik, E., Obalı, M., Yüksekışık, N., Öktemer, A., Pekel, T., İhsanoğlu, E. 1997. Denel Organik Kimya. A.Ü.F.F. Yayınları, 835 sayfa, Ankara.
Erdik,E. , Daşkapan,T. 2002. Can we aminate Grignard reagents under Barbier conditions ? Tetrahedron Lett. , 43 ; 6237-6239.
Espenson, J. H. 1995. Chemical kinetics and rection mechanisms . 2.Baskı , McGrow-Hill : New York.
Evans, D., Britton, T.C., Dorow, R.L., Dellaria, J.F. 1986. Stereoselective amination of chiral enolates. A new approach to the asymmetric synthesis of α- hydrazino and α - amino acid derivatives. J. Am. Chem. Soc., 108; 6395-6397.
Evans, D.A. , Evrard, D.A. , Rychnowsky, S.D. , Früh, T. , Wittingham, W.G. , deVries, K.M. 1992. A general approach to the asymmetric synthesis of vancomycin-related arylglycines by enolate aziridation. Tetrahedron Lett. , 33 ; 1189-1192.
Felix, C. , Laurent, A. , Lesniak, S. , Mison,P. 1991. The fluoromethyl ketone oximes and allylic Grignard reagent. J.Chem.Res. ,32 (5) ; 33.
Garst, M.E. , Lukton, D. 1980. Phenyldiazenes from phenyldiazonium fluoroborate and carbanions. Synth. Commun. 10; 155-160.
Genet, J. P. , Mallort, S. , Greek, C. , Piveteau, E. 1991. Electrophilic amination : First direct transfer of NHBoc with Li , t-buthyl-N-tosyloxycarbamate.
Tetrahedron Lett. , 32 ; 2359-2362.
Genet, J. P., Greck, C. , Bischoff, L. , Girard, A., Hajicek, J. 1994. Electrophilic amination of carbanions with metallated t-buthyl-N-tosyloxycarbamate. Bull.
Soc. Chem. Fr., 131; 429.
Genet, J.P., Mallart, S., Greck, C., Piveteau, E. 1991. Electrophilic amination: First direct transfer of NHBOC with Li, t-buthyl-N-tosyloxycarbamate. Tetrahedron Lett., 32; 2359-2362.
Gilman, H., Kirby, J.E., Keinney, C.R. 1929.The forced reaction of phenyl isothiocyanate and benzophenon anil with phenylmagnesium bromide. An unusual type of 1,4-addition to a conjugated system that is part aliphatic and part aromatic. J. Am. Chem.Soc. , 51, 2252-2261.
Girard, A. , Greek, C. , Ferroad, D. , Genet, J.P. 1996. Synthesis of the syn and anti α-amino-β-hydroxy acids of vancomycin : (2S,3R) and (2R,3R) p-chloro-3-hydroxytyrosines. Tetrahedron Lett. , 37 ; 7967-7970.
Goering, H L. , Kantner , S. , Seitz, Jr. E. P. 1985. Alkylation of allylic derivatives. 10.
Relative rates of reactions of allylic carboxylates with lithium dimethyl cuprates. J. Org. Chem. , 50 ; 5450-5499.
Greek, C. , Bischoff, L. ,Ferreira, F. , Pinel, C. , Genet, J.P. 1993. Asymmetric synthesis of anti N-Boc-α-hydrazino-β-hydroxyesters from β-ketoesters by sequential catalytic hydrogenation and electrophilic amination. Synth. Lett., 7 ; 475-477.
Guijarro, A. , Rieke, R. D. 1998. Structure- reactivity relationship in the reaction of highly reactive zinc with alkyl bromides. Angew. Chem. Int. Ed. , 37(12) ; 1679-1681.
Guijarro, A. , Rosenberg, D. M. ,Rreke, R. D. 1999. The reaction of active zinc with organic bromides. J. Am. Chem. Soc. , 121 ; 4155-4167.
Gynes, F. , Bergmann, K.E. , Welch, J. T. 1998. Convenient access to primary amines by employing the Barbier-type reaction of N-(trimethylsilyl)imines derved from aromatic and aliphatic aldehydes. J. Org. Chem. , 63 ; 2824-2828.
Hattori, K. , Maruoka, M. , Yamamato, H. 1982. Beckmann rearrangement of oxime sulfonates by Grignard reagents. Tetrahedron Letts. , 23 ; 3395-3396.
Henze, H.R. , Comption, W.D. 1957. Studies on the synthese of ethyleneimines from interaction of ketoxime and Grignard reagents. J.Org.Chem. , 23 ; 1036-1038.
Ho, C-H ., Lau, T.C. 2000. Copper-catalyzed amination of alkenes and ketones by phenylhydroxylamine. New J. Chem. ,(11) ; 859-863.
Hoch, J. 1936. Action des organomagnèsiens sur les cètoximes. Compt. Rend. , 203 ; 799-801.
Hoch, J. 1934. Action des organomagnèsiens sur les cètoximes. Compt. Rend. , 198 ; 1865-1868.
Hoch, J. 1937. Action des organomagnèsiens sur les trialcoylacètophenonoximes.
Compt. Rend. , 204 ; 358-360.
Hogopian, R.A. ,Terien, M.J. ,Murdoch, J.R. 1984. Synthesis of amines through nucleophilic addition on nitrogen. J. Am. Chem. Soc. ,106; 5753-5754
Huntress, E.H. , Carten, F.H. 1940. Identification of organic compounds. I.
Chlorosulfonic acid as a reagent for the identification of aryl halides.
J.Am.Chem.Soc. , 62 ; 511-514.
Huntress, E.H. ,Autenrieth, J.S. 1941. Identification of organic compounds, IV.
Chlorosulfonic acid as a reagent for identification of alkylbenzenes.
J.Am.Chem.Soc. , 63 ; 3346-3448.
Husek, P. 1991. Rapid derivatization and gas chromatographic determination of aminoacids. J. Chrom. B. , 552 ; 289-299.
Itsuno, S. , Miyazaki, K. , Ito, K. 1986. Reaction of aldehyde O-Alkyloxime with organometallic compounds. Tetrahedron Lett. , 27 ; 3033-3036.
Keller, R.N. , Wynocoff, H.D. 1946. Copper (I) chloride. Inorg. Synth. , 2 ; 1-4.
Kissman, H.M., Tarbel, D.S. ,Williams,J. 1953. 2,2’–Diphenyl-3,3’-dimethylethyleneimine and related compounds. J. Am. Chem. Soc. , 75 ; 2959 - 2962.
Kitamura, M. , Chiba. S. , Narasaka, K. 2003. Synthesis of primary amines and N-methylamines by the electrophilic amination of Grignard reagents with 2-imidazolidinone O-sulfonyl-oxime. Bull. Chem. Soc. Japan. ,76 ; 1063-1070.
Koçoğlu, M. 2002. Yüksek Lisans Tezi. A. Ü. Fen Fakültesi , 70 s. , Ankara.
Krause, N. 2002. Modern Organocopper Chemistry. Wiley- VCH , 377 s. , Mörlenbach.
Krause, N. 1999. New results regarding the structure and reactivity of cyanocuprates.
Angew. Chem. Int. Ed. . 38 ; 79-81.
Laurent, A. , Müller, A. 1969. Sterochimie de la synthese d’aziridines par action des magnesiens sur les cetoximes. Tetrahedron Lett. ; 759.
Leonard, J. , Lygo, B. , Procter; G. 1996. Advanced Practical Organic Chemistry.
Chapman and Hall , 294 s. , London.
Lipshutz, B.H. , Sengupta, S. 1992. Organocopper reagent. Substitution, conjugate addition , carbometallocupration and other reactions. Org. React. ; 135-631.
Lipshutz, B.H. 1997 . Downsizing copper in modern cuprate couplings. Acc. Chem.
Res. ,30 ; 277-282.
Maclin, K.M. , Richey, H.G. 2002.Hammett ρ of reactions of MeLi with benzophenones. J. Org. Chem. , 67 ; 4370-4371.
MacPhee, J.A. , Dubois, J.E. 1972. Ketones synthesis via the Grignard reagent-acid chloride condensation as catalyzed by cuprous chloride. An interesting structural requirement. Tetrahedron Lett. ; no:6 ; 467-470.
Maruoka, K. ,Yamamoto, H. 1985. Selective reactions using organoaluminium reagents.
Angew. Chem. Int. Ed. Engl. , 24 ; 668-682.
Matteson, D. S. 1974. Mechanism of organometallic reactions.
Mori, S., Aoyama, T., Shioiri, T. 1984. New methods and reagents in organic synthesis, 40. Amination of aromatic and heteroaromatic organometallics using diphenyl phosphorazide (DPPA). Tetrahedron Lett., 25(4); 429-432.
Mulzer, J. , Altenbach, H.J.I.,Braun, M. ,and Krohn, K.1991. Electrophilic Aminations.
Nakamura, E. , Yoshikai , N. 2004. On the rection mechanisms of ˝Higher Order Cuprate˝ , Alias ˝Lupshutz Cuprate˝ . Bull. Chem. Soc. Japan ,77 ; 1-12.
Namera, A. , Yashiki , M. ,Nishida , M. , Kojima , T. 2002. Direct extract derivatization for determination of aminoacids in human urine by gas chromatography and mass spectrometry. J. Chrom. B. , 776 ; 49-55.
Narasaka, K., Tsutsui, H., Hyashi, Y. 1997. Preparation of primary amines by the copper(I) catalyzed reaction of 4,4’-bis(trifluoromethyl) benzophenone O- methylsulfonyloxime and alkyl Grignard reagents. Chemistry Letters , 317-318.
Narasimhan, N.S., Ammanamanchi, R. 1983. A useful method to introduce ortho amino groups in aromatic compounds. Tetrahedron Letts., 24(43); 4733-4734.
Negishi, E. , King, A.O. ,Okukado, N. 1977. Selective C-C bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel –or palladium- catalyzed reaction of aryl – and benzyl – zinc derivatives with aryl halides. J. Org. Chem. 42(10), 1821-1823.
Nishiyama, K., Tanaka, N. 1983. Synthesis and reactions of trimethylsilylmethyl azide.
J.Chem. Soc. Chem. Commun.; 1322-1323.
Nomura, Y. , Anzai, H. 1958. New synthesis of azo compounds: Bromomethyl-azobenzenes. Bull. Chem. Soc. Japan, 79 ; 1648-1650.
Oguri, T. , Shiori, T. , Yamada, S. 1975. Aminoacids and peptides. Chem. Pharm.
Bull. Jpn. , 23(1) , 167-172.
Preffer, P.E. , Silbert, L.S. , Chirinko, J. M. 1972. α- Anions of carboxylic acids.II. The formation and alkylation of α-metalated aliphatic acids. J.Org.Chem., Vol:37,no:3 ; 451-457.
Prushnik, F. D. 1990. Organometallic chemistry of the transition elements. Plenum Press . New York
Radhakrishna, A.S., Laudon, G.M. ve Miller, M.J. 1979. Amination of ester enolates
Ricci, A. 2000. Modern amination methods. Wiley-VCH ,Weinheim.
Richey, H. G. , McLane, R. C. , Phillips, C. J. 1976. Reactions of oximes with organolithium compouns. Tetrahedron Lett. , 17 ; 233-234.
Rieke, R.D., Vlarde- Ortiz, R., Guijarro, A. 1998. Electrophilic amination of organozinc halides. Tetrahedron Lett., 39; 9157-9160.
Ruff, F. , Csizmadia, J.G. 1994. Organic reactions,equilibria,kinetics and mechanism.
Elsevier : New York.
Sakakura, T., Hara, M., Tanaka, M. 1994. Reaction of silyl enol ethers with arendiazonium salts. Part 2. - Amination of esters. J. Chem. Soc. Perkin Trans 1 ; 289-293.
Semon, W.L. 1923. The preparation of hydroxylamine hydrochloride and acetoxime.
J.Am.Chem.Soc. , 45 ; 188-190.
Semon, W.L. 1924. Hydroxylamine hydrochloride and acetoxime. Org.Synth.III. ; 61-64.
Shriver, D.F. 1969. The manipulation of air-sensitive compounds. McGraw-Hill .Chap.7.
Silverman, G.A. , Rakita, P.E. 1996. Handbook of Grignard Reagents. Marcel Dekker, 708 sayfa , New York.
Smulik, J. A. , Vedeys, A. 2003. Improved reagent for electrophilic amination of stabilized carbanions. Org. Lett. , 5(22) ; 4187-4190.
Sykes, P. 1975. Guidebook to mechanism in organic chemistry, Longmans , Chap.13.
Taylor, E.C., Sun, J.H.. 1980. A new synthesis of aminomalononitrile tosylate.
Synthesis; 801-802.
Taylor, R.J.K 1994. Organocopper Reagents. A Practical Approach. Oxford University Press, 362 sayfa, England.
Trimble, L.A., Vederas, J.C. 1986. Amination of chiral enolates by dialkyl azodiformates. Synthesis of α- hydrazino acids and α- amino acids. J. Am.
Chem. Soc., 108; 6397-6399.
Trost, B.M. , Pearson,W.H. 1983. Sulfur activation of azides toward addition of organometallics.Amination of aliphatic carbanions. J. Am. Chem. Soc. , 105(4); 1054-1056.
Tsutsui, H. 1999. Preparation of primary amines by the alkylation of O-sulfonyloximes of benzophenone derivatives with Grignard reagents. Bull. Chem. Soc. Japan.
,72 ; 1869-1878.
Vidal, J. , Guy, L. Sterin, S. , Collet, A. 1993. Electrophilic Amination: Preparation and use of N-boc-3-(4-cyanophenyl) oxaziridine. J. Org. Chem., 58 ; 4791-4793.
Wakefield, B.J. 1990. Organolithium Methods in Organic Synthesis. Academic Press, 189 sayfa, Florida.
Wakefield, B.J. 1995. Organomagnesium Methods in Organic Synthesis. Academic Press, 249 sayfa, Florida.
Watson, S.C. , Eastham, J.F. 1967. Colored indicators for simple direct titration of magnesium and lithium reagents. J. Organometal. Chem. , 9(1) ; 165-168.
Weissberger, A. 1981. Investigation of rates and mechanisms of reactions. Parts I and II, Vol: VI , Techniques of chemistry ,4. baskı , Wiley- Interscience:New York.
Yamataka, H. , Miyano, N. , Hanafusa, T. 1991. Comparative mechanistic study of the reactions of benzophenone with n-BuMgBr and n-BuLi. J. Org. Chem. , 56 ; 2573-2575.
Zheng, N. , Armstrong, J.D., III. McWilliams , J.C. , Valente, R.P. 1983.Asymetic synthesis of α-aminoacid derivatives via an electrophilic amination of chiral amide cuprates with Li t-buthyl-N-tosyloxycarbamate. Tetrahedron Lett., 38 ; 2817-2820.