SYNTHESIS AND THERMAL PROPERTIES OF NOVEL MALEONITRILES

Yıl 2016, Cilt: 34 Sayı: 2, 153 - 158, 01.06.2016

Ali Erdoğmuş

Öz

In this study, the synthesis and thermal properties of two novel maleonitriles bearing 8-membered heterocyclic derivatives is described first time. New maleonitriles, benzo-(1,2-bis-methylthio)maleonitrile and [Benzo-15-crown-5]-(4,5-bis-methylthio)maleonitrile have been prepared by the reaction of different alkyl halides such as 1,2-bis(brommethyl)benzene and 4,5-bis-(brommethyl)[benzo-15-crown-5] with dithiomaleonitrile disodium salt. Both compounds are characterized by IR, Mass, NMR spectroscopy as well as elemental analysis.

Anahtar Kelimeler

Macrocycle, maleonitrile, crown ethers, thermal properties.

Kaynakça

• [1] Blomquist A. T., Winslow E. C. J. Org. Chem. 1945, 10, 149-158.
• [2] Dewar M. J. S., Olivella S., Stewart J. J. P. J. Am. Chem. Soc. 1986, 108, 5771-5779.
• [3] Agmon N. J. Am. Chem. Soc. 1984, 106, 6960- 6962.
• [4] Dalton J. C., Wreide P. A., Turro N. J. J. Am. Chem. Soc. 1970, 92, 1318-1326.
• [5] Lewis F. M., Mayo F. J. Am. Soc. 1948, 70, 1529-1533.
• [6] Helling G., Woehrle D. Makromol. Chem. 1978, 179, 101-108.
• [7] Mommaerts H. Bull. Class Sci. Acad. Roy. Belg. 1943, 27, 576-579.
• [8] Rondestvedt C. S., Kalm M. J., Vogl O. J. Am. Chem. Soc. 1956, 78, 6109-6115.
• [9] Vogl O., Rondesvedt C. S. J. Am. Chem. Soc. 1956, 78, 3797-3799.
• [10] Glass R. S., Richard D., McConnell W. W. Organometallics 1984, 3, 1630-1632.
• [11] Kuwae R., Kawakami K., Tanaka T. Inorg. Chim. Acta 1977, 22, 39-42.
• [12] Kaneshima T., Yumoto Y., Kawakami K., Tanaka T. Inorg. Chim. Acta 1976, 18, 29- 34.
• [13] Lu H. S. M., Berson J. A. J. Am. Chem. Soc. 1997, 119, 1428-1438.
• [14] Kobayashi N., in: Kadish K. M.; K. M. (Eds.), The Porphyrine Handbook, vol. 2, Academic Press: New York, 2000; pp. 301.
• [15] Andersen K., Anderson M.; Anderson O. P., Baum S., Baumann T. F., Beall L. S., Broderick W. E., Cook A. S., Eichhorn D. M., Goldberg D., Hope H., Jarrell W., Lange S. J., McCubbin Q. J., Mani N. S., Miller T., Garrido Montalban A., Rodrigez-Morgade M. S., Lee S., Nie H., Olmstead M. M., Sabat M., J. W., Stern C., White A. J. P., Williams D. B. G., Williams D. J., Barrett A. G. M., Hoffman B. M. J. Heterocyclic Chem. 1998, 35, 1013-1042.
• [16] Koray A. R., Ahsen V., Bekaroğlu Ö . J. Chem. Soc., Chem. Commun. 1986, 932- 933.
• [17] van Nostrum C. F., Nolte R. J. M. Chem. Commun. 1996, 2385-2392.
• [18] Erdoğmuş A., Koca A., Avcıata U., Gül A. Z Anorg Chem. 2008, 634, 2649-2654.
• [19] Erdoğmuş A., Koca A., Avcıata U., Gül A. Pol J Chem. 2008, 82, 1541-1551.
• [20] Sesalan B. Ş., Gül A. Polyhedron 2003, 22, 3083-3090.
• [21] Takagi M., Ueno K. In: Vogtle F., Weber E. editors.Topics in current chemistry, host guest complex chemistry III. Springer: Berlin, 1984, pp. 39.
• [22] Katayama Y., Nita K., Ueda M., Nakamura H., Takagi M. Anal Chim Acta 1985, 173, 193-209.
• [23] Kaifer A., Gustowski D. A., Echegoyen L., Gotto V. J., Schultz R. A., Cleary T. P. et al. J Am Chem Soc. 1985, 107, 1958-1965.
• [24] Kimura K., Tanaka M., Kitazawa S., Shono T. Chem Lett. 1985, 8, 1239-1240.
• [25] Bartch R. A., Czech B. P., Kang S. I., Stewart L. E., Walkowiak W., Charewicz W. A. et al. J Am Chem Soc. 1985, 107, 4995-4997.
• [26] Nakashima K., Yamawaki Y., Nakatsuji S., Akiyama S., Kaneda T., Misumi S. Chem Lett. 1983, 1415-1418.
• [27] Bubnis B. P., Pacey G. E. Tetrahedron Lett. 1984, 25, 1107-1110.
• [28] Sesalan B. Ş., Gül A. Phosphorus, Sulfur 2003, 178, 2081-86.
• [29] Bahr G., Schleitzer G. Chem. Ber. 1967, 10, 8-26.
• [30] Witting G., Joos N., Ratheelder P. J. Am. Chem. Soc. 1957, 610, 151-187.
• [31] Luboch E., Cygon A., Liernat J. F. Tetrahedron 1990, 46, 2461-2472.