Preparation of Liquid-Crystalline Diacetylenes Using Coupling Reactions of Alkynyliodonium Salts with Alkynylcopper Reagents

Chi-Han Lee; No-Hee Jeong; Ki-Dae Nam; Tsugio Kitamura

Journal of Industrial and Engineering Chemistry, Vol.5, No.1, 40-44, March, 1999

Chi-Han Lee^†, No-Hee Jeong, Ki-Dae Nam, and Tsugio Kitamura¹

Department of Industrial and Engineering Chemistry, Chungbuk National University, Cheong-Ju 361-763, Korea
¹Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University, 36 Hakozaki, Fukuoka 812, Japan

E-mail:

Alkynyl(phenyl)iodonium tosylates with long alkoxy chains, such as (dodecyloxy)-and (tetradecyloxy)phenyl groups are prepared and reacted with aryl-substituted alkynylcopper reagents. The coupling reaction proceeded under mild conditions and provided unsymmetrical and symmetrical diacetylenes. The selectivity of the formation of these diacetylenes was dependent on the substituent on the alkynylcopper reagents. The diacetylenes prepared here displaced mesogenic properties.

Keywords:alkynyl(phenyl)iodonium tosylates;copper reagent;coupling reaction;diacetylenes;liquid crystal

[References]

Varvoglis A, The Organic Chemistry of Polycoordinated Iodine, VCH Publisher, New York (1992)
Moriarty RM, Vaid RK, Synthesis, 431 (1990)
Ochiai M, Rev. Heteroatom Chem., 2, 92 (1989)
Maletina II, Orda VV, Yagupolskii LM, Russ. Chem. Rev., 58, 544 (1989)
Merkushev EB, Russ. Chem. Rev., 56, 826 (1989)
Moriarty RM, Prakash O, Acc. Chem. Res., 19, 244 (1986)
Varvoglis A, Synthesis, 709 (1984)
Koser GF, The Chemistry of Functional Groups; Supplement D; Patai S.; Rappoport, Z., Eds.; Wiley: New York, Chapt. 18 and 25 (1983)
Umemoto T, Yuki Gosei Kagaku Kyokai Shi, 41, 251 (1983)
Stang PJ, Angew. Chem.-Int. Edit., 31, 274 (1992)
Stang PJ, Acc. Chem. Res., 24, 304 (1991)
Stang PJ, Acc. Chem. Res., 24, 304 (1991)
Stang PJ, Kitamura T, J. Am. Chem. Soc., 109, 7561 (1987)
Kitamura T, Tanaka T, Taniguchi H, Stang PJ, J. Chem. Soc.-Perkin Trans. 1, 1, 2892 (1991)
Wang MD, Monahan S, Liptak D, Vohra R, SPIE, 29, 1911 (1993)
Wu ST, Margerum JD, Hsu CS, Lung SH, Appl. Phys. Lett., 61, 630 (1992)
Stiegman AE, Graham E, Perry KJ, Khundkar LR, Cheng LT, Perry JW, J. Am. Chem. Soc., 113, 7658 (1991)
Milburn W, Campbell C, Shand AJ, Werninck AR, Liq. Cryst., 8, 623 (1990)
Fouquey C, Lehn JM, Malthete J, J. Chem. Soc.-Chem. Commun., 1424 (1987)
Grant B, Mol. Cryst. Liq. Cryst., 48, 175 (1978)
Stang PJ, Surber BW, Chen ZC, Roberts KA, Anderson AG, J. Am. Chem. Soc., 109, 228 (1987)
Rebrovic L, Koser GF, J. Org. Chem., 49, 4700 (1984)
Lipshutz BH, Sengupta S, Org. React., 41, 135 (1992)
Seto K, Shimojitosho H, Jpn. Kokai Tokkyo Koho JP 01,197,451; Chem. Abstr., 112, 76593x (1990)

[Referenced By]

[1] Varvoglis A, The Organic Chemistry of Polycoordinated Iodine, VCH Publisher, New York (1992)

[2] Moriarty RM, Vaid RK, Synthesis, 431 (1990)

[3] Ochiai M, Rev. Heteroatom Chem., 2, 92 (1989)

[4] Maletina II, Orda VV, Yagupolskii LM, Russ. Chem. Rev., 58, 544 (1989)

[5] Merkushev EB, Russ. Chem. Rev., 56, 826 (1989)

[6] Moriarty RM, Prakash O, Acc. Chem. Res., 19, 244 (1986)

[7] Varvoglis A, Synthesis, 709 (1984)

[8] Koser GF, The Chemistry of Functional Groups; Supplement D; Patai S.; Rappoport, Z., Eds.; Wiley: New York, Chapt. 18 and 25 (1983)

[9] Umemoto T, Yuki Gosei Kagaku Kyokai Shi, 41, 251 (1983)

[10] Stang PJ, Angew. Chem.-Int. Edit., 31, 274 (1992)

[11] Stang PJ, Acc. Chem. Res., 24, 304 (1991)

[12] Stang PJ, Acc. Chem. Res., 24, 304 (1991)

[13] Stang PJ, Kitamura T, J. Am. Chem. Soc., 109, 7561 (1987)

[14] Kitamura T, Tanaka T, Taniguchi H, Stang PJ, J. Chem. Soc.-Perkin Trans. 1, 1, 2892 (1991)

[15] Wang MD, Monahan S, Liptak D, Vohra R, SPIE, 29, 1911 (1993)

[16] Wu ST, Margerum JD, Hsu CS, Lung SH, Appl. Phys. Lett., 61, 630 (1992)

[17] Stiegman AE, Graham E, Perry KJ, Khundkar LR, Cheng LT, Perry JW, J. Am. Chem. Soc., 113, 7658 (1991)

[18] Milburn W, Campbell C, Shand AJ, Werninck AR, Liq. Cryst., 8, 623 (1990)

[19] Fouquey C, Lehn JM, Malthete J, J. Chem. Soc.-Chem. Commun., 1424 (1987)

[20] Grant B, Mol. Cryst. Liq. Cryst., 48, 175 (1978)

[21] Stang PJ, Surber BW, Chen ZC, Roberts KA, Anderson AG, J. Am. Chem. Soc., 109, 228 (1987)

[22] Rebrovic L, Koser GF, J. Org. Chem., 49, 4700 (1984)

[23] Lipshutz BH, Sengupta S, Org. React., 41, 135 (1992)

[24] Seto K, Shimojitosho H, Jpn. Kokai Tokkyo Koho JP 01,197,451; Chem. Abstr., 112, 76593x (1990)