Syntheses of Novel Macrocyclic Ethers Containing Nitro Groups

Seung Hyun Chang; Sang Chil Moon; Hak Hee Kim; Kwang Bo Chung

Journal of Industrial and Engineering Chemistry, Vol.4, No.3, 211-214, September, 1998

Export Citation

Syntheses of Novel Macrocyclic Ethers Containing Nitro Groups

Seung Hyun Chang^†, Sang Chil Moon, Hak Hee Kim¹, and Kwang Bo Chung²

Department of Chemistry, Taegu University, Kyungsan 712-714, Korea
¹Division of Chemical Engineering, Sun Moon University, Asan 336-840, Korea
²Department of Chemical Engineering, Hanseo University, Seosan 356-820, Korea

E-mail:

The macrocyclic polyether, 1,30; 6,1l; 13,18; 23,28-tetrabenzo-9,15,26,32-tetra-nitro-2,5,19,22-tetraoxacyclotetratriacontane 1 and 1,36; 9,14; 16,21; 29,34-tetra-benzo-12,18,32,38-tetranitro-2,5,8,22,25,28-hexaoxacyclotetracontane 2 have been synthesized by the reaction of 2,2'-methylenebis (4,4'-nitro-phenol) 3 with 1,2-dichloro-ethane and bis(2-chloroethyl)ether respectively in the presence of NaOBu-t and t-BuOH. The macrocyclic polyethers were purified by chromatography and recrystallization.

Keywords:macrocyclic polyether;2;2’-methylenebis(4;4’-nitrophenol);1;2-dichloro-ethane;bis(2-chloroethyl)ether

[References]

Bradshaw JS, Stott PE, Tetrahedron, 36, 461 (1980)
Izatt RM, Christensen JJ, Synthetic Multidentate Macrocyclic Compound, Academic Press, New York, San Francisco, London (1978)
Pedersen CJ, Frensdorf DJ, Angew. Chem.-Int. Edit., 11, 16 (1972)
Newcomb M, Cram DJ, J. Am. Chem. Soc., 97, 1257 (1975)
Chang SH, Yoon MH, Kim CS, Chung KB, Shim JH, J. Korean Chem. Soc., 33, 651 (1989)
Chang SH, Kim DJ, Absts, 9th International Conference on Organic Syntehsis, June 28-July 2, Montreal, Canada, 100 (1992)
Chang SH, Kim JY, J. Korean Chem. Soc., 38, 377 (1994)
Chang SH, Kim DJ, Kim JY, Lee KD, J. Korean Chem. Soc., 33, 254 (1989)
Lee DK, Lee IC, Kim JY, Chang SH, Han SH, Cha GS, J. Korean Chem. Soc., 38, 529 (1994)
Chang SH, Kim JY, Yeon AS, Cha GS, Smid J, Absts, 8th International Symposium on Molecular Recognition and Inclusion, July 31-August 5, Ottawa, Canada, 97 (1994)
Chang SH, Kim TY, Chung KB, J. Korean Chem. Soc., 40, 635 (1996)
Chattaway FD, Goep RM, J. Chem. Soc., 699 (1933)
Bohmer V, Lotz W, Org. Prep. Proce. Int., 7, 243 (1975)
Burden IJ, Coxon AC, Stoddart JF, Wheatley CM, J. Chem. Soc.-Perkin Trans. 1, 220 (1977)
Stoddart JF, Wheatley CM, J. Chem. Soc.-Chem. Commun., 390 (1974)
Pedersen CJ, J. Am. Chem. Soc., 89, 7017 (1967)
Ungaro R, Smid J, J. Am. Chem. Soc., 98, 5198 (1976)
Kime DE, Norymberski JK, J. Chem. Soc.-Perkin Trans. 1, 1408 (1977)

[1] Bradshaw JS, Stott PE, Tetrahedron, 36, 461 (1980)

[2] Izatt RM, Christensen JJ, Synthetic Multidentate Macrocyclic Compound, Academic Press, New York, San Francisco, London (1978)

[3] Pedersen CJ, Frensdorf DJ, Angew. Chem.-Int. Edit., 11, 16 (1972)

[4] Newcomb M, Cram DJ, J. Am. Chem. Soc., 97, 1257 (1975)

[5] Chang SH, Yoon MH, Kim CS, Chung KB, Shim JH, J. Korean Chem. Soc., 33, 651 (1989)

[6] Chang SH, Kim DJ, Absts, 9th International Conference on Organic Syntehsis, June 28-July 2, Montreal, Canada, 100 (1992)

[7] Chang SH, Kim JY, J. Korean Chem. Soc., 38, 377 (1994)

[8] Chang SH, Kim DJ, Kim JY, Lee KD, J. Korean Chem. Soc., 33, 254 (1989)

[9] Lee DK, Lee IC, Kim JY, Chang SH, Han SH, Cha GS, J. Korean Chem. Soc., 38, 529 (1994)

[10] Chang SH, Kim JY, Yeon AS, Cha GS, Smid J, Absts, 8th International Symposium on Molecular Recognition and Inclusion, July 31-August 5, Ottawa, Canada, 97 (1994)

[11] Chang SH, Kim TY, Chung KB, J. Korean Chem. Soc., 40, 635 (1996)

[12] Chattaway FD, Goep RM, J. Chem. Soc., 699 (1933)

[13] Bohmer V, Lotz W, Org. Prep. Proce. Int., 7, 243 (1975)

[14] Burden IJ, Coxon AC, Stoddart JF, Wheatley CM, J. Chem. Soc.-Perkin Trans. 1, 220 (1977)

[15] Stoddart JF, Wheatley CM, J. Chem. Soc.-Chem. Commun., 390 (1974)

[16] Pedersen CJ, J. Am. Chem. Soc., 89, 7017 (1967)

[17] Ungaro R, Smid J, J. Am. Chem. Soc., 98, 5198 (1976)

[18] Kime DE, Norymberski JK, J. Chem. Soc.-Perkin Trans. 1, 1408 (1977)