• Sonuç bulunamadı

38

Şekil 29 : 3,4-dimetoksi benzaldoksim (1a) Bileşiğinin FT-IR spektrumu

39

Şekil 30 : 3,4-dimetoksi benzaldoksim (1a) Bileşiğinin CDCl3 de 1H NMR Spektrumu

40

1a Bileşiğinin CDCl3 de 101 MHz 13C spektrumu

Şekil 31 : 3,4-dimetoksi benzaldoksim (1a) CDCl3 de 101 MHz 13C Spektrumu

-10

41

Şekil 32: p-Tolualdoksim (1b) Bileşiğinin FT-IR spektrumu

42

43

Şekil 34: p-Tolualdoksim (1b) Bileşiğinin CDCl3 de 101 MHz 13C Spektrumu

44

Şekil 35: Benzaldoksim (1c) Bileşiğinin FTIR Spektrumu

45

Şekil 36: Benzaldoksim (1c) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

46

Şekil 37: Benzaldoksim (1c) Bileşiğinin CDCl3 de 101 MHz 13C Spektrumu

47

Şekil 38: p-Klorobenzaldoksim (1d) Bileşiğinin FT-IR Spektrumu

48

Şekil 39: p-Klorobenzaldoksim (1d) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

49

Şekil 40: p-Klorobenzaldoksim (1d) Bileşiğinin CDCl3 de 101 MHz 13C Spektrumu

50

Şekil 41: p-Nitrobenzaldoksim (1d) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

51

Şekil 42: p-Nitrobenzaldoksim (1d) Bileşiğinin CDCl3 de 101 MHZ 13C Spektrumu

52

Şekil 43: Asetofenon oksim (1f) Bileşiğinin FT-IR Spektrumu

53

54

55

56

57

Şekil 48: Siklopentanon oksim (1h) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

58

Şekil 49: Siklopentanon oksim (1h) Bileşiğinin CDCl3 de 101 MHz 13C NMR Spektrumu

59

60

61

Şekil 52: Aseton oksim (1j) Bileşiğinin FT-IR Spektrumu

62

Şekil 53: 3,4-dimetoksi benzaldehid (2a) Bileşiğinin FT-IR Spektrumu

63

Verim: 0.040 / 0.050* 100= %80

Şekil 54: p-Tolualdehid (2b) Bileşiği GC-MS Kantitatif Analiz Sonucu

64

Şekil 55: p-Tolualdehid (2b) Bileşiği Kütle Spektrumu

65

Verim: 0.025 / 0.050 * 100 = %50

Şekil 56: Benzaldehid (2c) Bileşiğinin GC-MS Kantitatif Analiz Sonucu

66

Şekil 57: Benzaldehid (2c) Bileşiğinin Kütle Spektrumu

67

68

Şekil 58: p-Kloro benzaldehid (2d) Bileşiğinin FT-IR Spektrumu

240 260 280 PROTON_02 300

NH-56

69

70

Şekil 60: p-Nitro benzaldehid (2e) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

71

Şekil 61: Asetofenon (2f) Bileşiğinin FT-IR Spektrumu

72

Şekil 62: Asetofenon (2f) Bileşiğinin CDCl3 de 400 MHz 1H NMR Spektrumu

73

Şekil 63: Fenasil bromür (2g) Bileşiğinin FT-IR Spektrumu

74

75

Verim: 0.024 / 0.05 * 100 = %48

Şekil 65: Siklopentanon (2h) Bileşiğinin GC-MS Kantitatif Analiz Sonucu

76

Şekil 66: Siklopentanon (2h) Bileşiğinin Kütle Spektrumu

77

Verim: 0.038 / 0.050 * 100 = %76

Şekil 67: Siklohekzanon (2i) Bileşiğinin GC-MS Kantitatif Analiz Sonucu

78

Şekil 68: Siklohekzanon (2i) Bileşiğinin Kütle Spektrumu

79

Verim: 0.042 / 0.050 * 100 = %84

Şekil 69: Aseton (2j) Bileşiğinin GC-MS Kantitatif Analiz Sonucu

80

Şekil 70: Aseton (2j) Bileşiğinin Kütle Spektrumu

81

KAYNAKLAR

1) Singh, R.B., Garg, B. S., Singh, R. P. Oximes as Spectrophotometric Reagents A Review. Tetrahedron, 26, 425-44 1979.

2) Migrdichian, V. Organic Synthesis, Open-Chain Saturated Compounds. Reinhold Pub. Corp., New York. 1957.

3) Jerslev, B. Crystal Structure of Oximes. Nature, 180, 1410- 12. 1957.

4) Smith, P.A.S. The Chemistry of Open-Chain Organic Nitrogen Compounds. 2, 29-68, New York 1966.

5) Alma García-O., Abdessamad G., Edilso R., Hermenegildo G. Mixed (Fe2+ and Cu2+) double metal hexacyanocobaltates as solid catalyst for the aerobic oxidation of oximes to carbonyl compounds. Journal of Catalysis 311 386–392 2014

6) Highly efficient aerobic oxidation of oximes to carbonyl compounds

catalyzed by metalloporphyrins in the presence of benzaldehyde. Xian-Tai Z., Qiu-Lan Y., Hong-Bing J. Tetrahedron Letters 51 613–617 2010

7) Liangyou H. and C. Akira H. Preparative Conversion of Oximes to Parent Carbonyl Compounds by Cerium(IV) Sulfate in Acetonitrile and Alcohol. Appl.

Organometal. Chem. 13, 867–869 1999

8) Corey, E. J.; Richman, J. E. Reaction of oxime O-acetates with chromous acetate.

Method for the conversion of ketoximes to ketones under mild conditions. J. Am.

Chem. Soc. 92, 5270 1970

9) Aizpuruna, J. M.; Palomo, C.; Chlorotrimethylsilane / Chromium (VI) reagents as new and versatile oxidation systems. Tetrahedron Lett. 24, 4367-4370 1983

10) Corey, E. J.; Suggs, J. W. Pyridinium chlorochromate An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds Tetrahedron Lett. Vol. 16 issue 31 2647-2650 1975

11) Chaudhuri, M. K.; Dehury, S. K.; Dhar, S. S.; Sinha, U. B. The economic synthesis of pyridinium fluoro chromate(VI) C5H5NH[CrO3F] (PFC) and solvent-free oxidation of organic substrates with PFC. Synth. Commun. 34, 4077 2004

12) Sadeghi, M.M.; Baltork, I. M.; Azaram, M.; Mazidi, M. R.; Regeneration of carbonyl compounds from oximes, phenylhydrazones, p-nitrophenylhydrazones and semicarbazones by quinolium dichromate under non aqueous conditions. Synth.

Commun. 31, 435-438 2001

82

13) D. Subhas B. and A. Venkat N.; Quinolium fluorochromate: An efficient reagent for the cleavage of C=N of oximes and hydrazones. Synthetic Communications 30 (6),1153- 1158 2000.

14) Drabowicz, J. Rapid deoximation with pyridinium chlorochromate-hydrogen peroxide system. Synthesis Issue 2 125-126 1980

15) Mohammadpoor B.; Pouranshirvani, S. 3-Carboxypyridinium Chlorochromate:

An Inexpensive and Efficient Reagent for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition. Synth. Commun, 26 1 1996

16) Aizpuruna, J. M:; Juaristi, M.;Leccea, B.; Palomo, Reagents and synthetic methods-40 : Halosilanes/chromium trioxide as efficient oxidizing reagents C.

Tetrahedron 41, 2903-2911 1985

17) Jong, G. L.; Kwak, K. H.; Hwang, J. P. Regeneration of aldehydes and ketones from oximes using bis(trimetilsiliyl)chromate. Synth. Commun. 22, 2425-2429 1992

18) Bendale, PM; Khadilkar, BM . Silica gel supported chromium trioxide: An efficient reagent for oxidative cleavage of oximes to carbonyl compounds under mild condition Synthetic Communications Vol. 30 Issue: 4 Pages: 665-669 2000

19) Hosseinzadeh, R.; Tajbakhsh, M.; Niaki, Y. M. 2,6-Dicarboxypyridinium chlorochromate: a mild, efficient, and selective reagent for oxidative deprotection of oximes to carbonyl compounds Tetrahedron Lett., 43, 9413-9416 2002

20) Pravin M. B., Bhushan M. K., Microwave promoted regeneration of carbonyl compounds from oximes using silica supported chromium trioxide Tetrahedron Letters, Volume 39, Issue 32, Pages 5867-5868 1998

21) Nemai C. Ganguly, Arun K. Sukai, Sripada De, and Prithwiraj De. Oxidative deprotection of oximes using pyridiniumfluorochromate and hydrogen peroxide. Syn.

Communications 31 (10) 1607-1612 2001

22) Ramin Ghorbani V., Ardeshir K. Phosphorus, Sulfur, and Silicon and the Related Elements Poly[N-(4-pyridiniumdichromate)-p-styrenesulphonamide] as an efficient reagent fort he cleavage of C=N bonds of oximes 179:1 55-59 2004

23) Surya Kanta De. A Mild and Efficient Method for Cleavage of C=N Using Imidazolium Dichromate Synthetic Communications 34(15) 2751-2755 2004

24) Ji-Dong L., Xiu Lian L., Li-Hong H., Changhe Z., Qiang W., and Xiao-Nan Z., Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2011 41, 1278–1281

25) Fang Lin A , Jianan Lin A , Wenjin Zheng A , Xiu Lian Lu A & Ji-Dong Lou Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 43:1518–1520, 2013

83

26) Ji-Dong L., Fang L., Xiu Lian L, Qiang W, and Xiao-Nan Z. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42:282–284, 2012 27) M. Somi Reddy, M. Narender, and K. Rama Rao. Synthetic Communications Vol. 34, No. 21, pp. 3875–3881, 2004

28) Ji-Dong L., Fang L., Lihong H., and Xiao-Nan Z. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42:1027–1029, 2012

29) Habib Firouzabadi A , Nasser Iranpoor A & Kamal Amani. Synthetic Communications Vol. 34, No. 19, pp. 3587–3593, 2004

30) Chaudhari, S. S.; Akamanchi, K. G.; Tetrahedron Lett. 39, 3209. 1998 31) Vikas N. T. Synthetic Communications, 35: 2827–2829, 2005

32) Fener C., Anchang L., Qiongjiao Y., Mingxing L., Daoming Z., and Lanying S.

Synthetic Communications, 29(6), 1049-1056, 1999

33) Zheng L., Run‐Bo D., Yu‐Lin X., & Sheng‐Yi S. Synthetic Communications, 35:

2515–2520, 2005

37) Ardeshir K. & Amin R. Organic Preparations and Procedures International 38:5, 484-490, 2006

38) Smith, J., Heidema, J. and Kaiser E., J. Am. Chem. Soc. 27 9274, 1972 39) J. R. Major and A. S. P. Azzoz. J. Chem. Soc. Faraday, Trans I, 79. 765. 1983

84

85

86

87

88

89

90

91

92

93

Benzer Belgeler