Novel Synthesis of Liquid-Crystalline 1,3-Butadiynes Using Coupling Reaction of Alkynyliodonium Salts with Organocopper Reagents

Chi-Han Lee; No-Hee Jeong; Seung-Woo Lee; Tsugio Kitamura

Journal of Industrial and Engineering Chemistry, Vol.3, No.2, 155-159, June, 1997

Chi-Han Lee, No-Hee Jeong¹, Seung-Woo Lee, and Tsugio Kitamura

Department of Chemical Science and Technology, Faculty of Engineering, Kyushu University, Fukuoka 812-81, Japan
¹Department of Industrial Chemistry, Chungbuk National University, Cheong-ju 361-763, Korea

The coupling reaction of alkynyl(phenyl)iodonium salts with alkynylcopper reagents proceeds under mild conditions to provide unsymmetrical and symmetrical 1,3-butadiynes. The length of the alkyl chains both in the alkynyl(phenyl)iodonium salts and in the copper reagents is not a significant factor of the coupling reaction and the unsymmetrical 1,3-butadiynes are selectively prepared. The prepared 1,3-butadiynes show mesogenic properties.

[References]

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Moriarty RM, Vaid RK, Synthesis, 431 (1990)
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[1] Kitamura T, J. Syn. Org. Chem., 53, 893 (1995)

[2] Varvoglis A, The organic Chemistry of Poly Coordinated Iodine; VCH Publisher: New York (1992)

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

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

[5] Stang PJ, Accounts Chem. Res., 24, 304 (1991)

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

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

[8] Kitamura T, Lee CH, Taniguchi H, Matsumoto M, Sano Y, J. Org. Chem., 59, 8053 (1994)

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

[10] Wu ST, Margerum JD, Hsu CS, Lung SH, Appl. Phys. Lett., 61, 6308 (1992)

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

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

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

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

[15] Schmidt G, Pure Appl. Chem., 27, 647 (1971)

[16] Vincett S, Roberts GG, Thin Solid Films, 68, 135 (1980)

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

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

[19] VanderVeen J, DeJeu WH, Grobben AH, Boven J, Mol. Cryst. Liq. Cryst., 17, 291 (1972)