Coupling reaction of alkynyliodonium salts with alkynylcopper reagents. A new access to liquid-crystalline 1,3-butadiynes

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals

Volumn 287, Issue , 1996, Pages 93-100

  Kitamura, T ^a   Lee, C H ^a   Taniguchi, Y ^a   Fujiwara, Y ^a   Sano, Y ^b   Matsumoto, M ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b KYUSHU SANGYO UNIVERSITY   (Japan)

Author keywords

1,4 disubstituted 1,3 butadiynes; Alkynyliodonium salts; Coupling reaction; Liquid crystals

Indexed keywords

COPPER COMPOUNDS; IODINE COMPOUNDS; SALTS; SYNTHESIS (CHEMICAL);

ALKYNYLCOPPER REAGENTS; ALKYNYLIODONIUM SALTS; COUPLING REACTIONS;

LIQUID CRYSTALS;

EID: 0030417012     PISSN: 1058725X     EISSN: None     Source Type: Journal    
DOI: 10.1080/10587259608038746     Document Type: Article

References (25)

1. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
2. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
3. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
4. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
5. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
6. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
7. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
8. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
9. For recent reviews and a book: (a) T. Kitamura, J. Synth. Org. Chem. Jpn., 53, 893 (1995). (b) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine (VCH Publisher, New York, 1992). (c) R. M. Moriarty and R. K. Vaid. Synthesis, 431 (1990). (d) M. Ochiai, Rev. Heteroatom Chem., 2, 92 (1989). (e) I. I. Maletina, V. V. Orda, and L. M. Yagupolskii, Russ. Chem. Rev. (Engl. Transl.), 56, 826 (1989). (g) R. M. Moriarty, and O. Prakash, Acc. Chem. Res., 19, 244 (1986). (h) A. Varvoglis, Synthesis, 709 (1984). (i) G. F. Koser, The Chemistry of Functional Groups; Supplement D, (Wiley: New York, 1983), eds., S. Patai and Z. Rappoport, Chaps. 18 and 25. (j) T. Umemoto, J. Synth. Org. Chem. Jpn., 41, 251 (1983).
10. P. J. Stang, Angew. Chem. Int. Ed. Engl., 1992, 31, 274; Acc. Chem. Res., 24, 304 (1991).
11. P. J. Stang, Angew. Chem. Int. Ed. Engl., 1992, 31, 274; Acc. Chem. Res., 24, 304 (1991).
12. P. J. Stang, T. Kitamura, J. Am. Chem. Soc., 109, 7561 (1987).
13. T. Kitamura, T. Tanaka, H. Taniguchi, P. J. Stang, J. Chem. Soc., Perkin Trans. 1, 2892 (1991); T. Kitamura, C. H. Lee, H. Taniguchi, M. Matsumoto, Y. Sano, J. Org. Chem., 59, 8053 (1994).
14. T. Kitamura, T. Tanaka, H. Taniguchi, P. J. Stang, J. Chem. Soc., Perkin Trans. 1, 2892 (1991); T. Kitamura, C. H. Lee, H. Taniguchi, M. Matsumoto, Y. Sano, J. Org. Chem., 59, 8053 (1994).
15. M. D. Wand, S. Monahan, D. Liptak, R. Vohra, SPIE, 1911, 299 (1993).
16. S. T. Wu, J. D. Margerum, C. S. Hsu, S. H. Lung, Appl. Phys. Lett., 61 630 (1992).
17. A. E. Stiegman, E. Graham, K. J. Perry, L. R. Khundkar, L.-T. Cheng, J. W. Perry, J. Am. Chem. Soc., 113, 7658 (1991).
18. G. H. W. Milburn, C. Campbell, A. J. Shand, A. R. Werninck, Liq. Crysts., 8, 623 (1990).
19. C. Fouquey, J.-M. Lehn, J. Malthete, J. Chem. Soc., Chem. Commun., 1424 (1987).
20. B. Grant, Mol. Cryst. Liq. Cryst., 48, 175 (1978).
21. H.-H. B. Meng, L. R. Dalton, S.-T. Wu, Mol. Cryst. L. Cryst., 250, 303 (1994).
22. G. Schmidt, Pure Appl. Chem., 27, 647 (1971); P. S. Vincett G. G. Roberts, Thin Solid Films, 68, 135 (1980).
23. G. Schmidt, Pure Appl. Chem., 27, 647 (1971); P. S. Vincett G. G. Roberts, Thin Solid Films, 68, 135 (1980).
24. P. J. Stang, B. W. Surber, Z.-C. Chen, K. A. Roberts, A. G. Andersen, J. Am. Chem. Soc., 109, 228 (1987); L. Rebrovic G. F. Koser, J. Org. Chem., 49, 4700 (1984).
25. P. J. Stang, B. W. Surber, Z.-C. Chen, K. A. Roberts, A. G. Andersen, J. Am. Chem. Soc., 109, 228 (1987); L. Rebrovic G. F. Koser, J. Org. Chem., 49, 4700 (1984).