Long-range chiral induction in chemical systems with helical organization. Promesogenic monomers in the formation of poly(isocyanide)s and in the organization of liquid crystals

Journal of the American Chemical Society

Volumn 120, Issue 36, 1998, Pages 9126-9134

  Amabilino, David B ^a   Ramos, Elena ^a   Serrano, José Luis ^b   Sierra, Teresa ^b   Veciana, Jaume ^a  

^a INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FORMAMIDE; MONOMER; POLY(ISOCYANIDE); POLYMER; SOLVENT; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; HYDROGEN BOND; LIQUID CRYSTAL; POLYMERIZATION;

EID: 0032537987     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980474m     Document Type: Article

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71. For discussions on CD, see: (a) Analytical Applications of Circular Dichroism; Purdie, N.; Brittain H. G., Eds.; Techniques and Instrumentation in Analytical Chemistry; Elsevier: Amsterdam, The Netherlands, 1994; Vol. 14. (b) Circular Dichroism, Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; VCH: Weinheim, 1994. (c) Rodger, A.; Nordén, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, 1997.
72. For discussions on CD, see: (a) Analytical Applications of Circular Dichroism; Purdie, N.; Brittain H. G., Eds.; Techniques and Instrumentation in Analytical Chemistry; Elsevier: Amsterdam, The Netherlands, 1994; Vol. 14. (b) Circular Dichroism, Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; VCH: Weinheim, 1994. (c) Rodger, A.; Nordén, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, 1997.
73. For discussions on CD, see: (a) Analytical Applications of Circular Dichroism; Purdie, N.; Brittain H. G., Eds.; Techniques and Instrumentation in Analytical Chemistry; Elsevier: Amsterdam, The Netherlands, 1994; Vol. 14. (b) Circular Dichroism, Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; VCH: Weinheim, 1994. (c) Rodger, A.; Nordén, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, 1997.
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75. The CD of related chiral poly(quinoxaline-2,3-diyl)s display similar bands, see: (a) Ito, Y.; Ihara, E.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509-1510. (b) Ho, Y.; Kojima, Y.; Murakami, M. Tetrahedron Lett. 1993, 34, 8279-8282. (c) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188-9189.
76. The CD of related chiral poly(quinoxaline-2,3-diyl)s display similar bands, see: (a) Ito, Y.; Ihara, E.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509-1510. (b) Ho, Y.; Kojima, Y.; Murakami, M. Tetrahedron Lett. 1993, 34, 8279-8282. (c) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188-9189.
77. It is unlikely that the chiral group attached to one extreme of the promesogenic unit could influence the electronic transition associated with the Cotton effect of the iminomethylene chromophore of the polymer backbone.
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79. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
80. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
81. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
82. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
83. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
84. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
85. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
86. For discussions concerning the twist between the component aromatic rings in benzylidineaniline derivatives, see: (a) Brocklehurst, P. Tetrahedron 1962, 18, 299-304. (b) Smith, W. F. Tetrahedron 1963, 19, 445-454. (c) Bürgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764. (d) van der Veen, J.; Grobben, A. H. In Liquid Crystals 3; Brown, G. H., Labes, M. M., Eds.; Gordon & Breach: New York, 1972; Vol. II, pp 589-595. (e) Bar, I.; Bernstein, J. Tetrahedron 1987, 43, 1299-1305. (f) Clegg, W.; Elsegood, M. R. J.; Heath, S. L.; Houlton, A.; Shipman, M. A. Acta Crystallogr. C. 1996, 52, 2548-2552. (g) Navon, O.; Bernstein, J. Struct. Chem. 1997, 8, 3-11. For an example of an X-ray crystal structure of a mesogen incorporating both phenyl benzoate and benzylideneaniline moieties, see: (h) Baumeister, U.; Hartung, H.; Gdaniec, M. Acta Crystallogr. C. 1987, 43, 1117-1119.
87. Bidan, G.; Guillerez, S.; Sorokin, V. Adv. Mater. 1996, 8, 157-160.
88. This view contrasts with that expressed concerning much lower molecular mass poly(phenylisocyanide) prepared in MeOH. See: Huang, J.-T.; Sun, J.; Euler, W. B.; Rosen, W. J. Polym. Sci. A. Polym. Chem. 1997, 35, 439-446.
89. (a) Stegemeyer, H.; Mainush, K. J. Chem. Phys. Lett. 1970, 6, 5-6.
90. (b) Stegemeyer, H.; Mainush, K. J. Naturwissenschaften 1971, 58, 599-602.
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93. (a) Li, J.; Takezoe, H.; Fukuda, A.; Watanabe, J. Liq. Cryst. 1995, 18, 239-250.
94. (b) Yamada, K.; Takanishi, Y.; Ishikawa, K.; Takezoe, H.; Fukuda, A.; Osipov, M. A. Phys. Rev. E 1997, 56, R43-R46.
95. For discussions concerning the twist between the component aromatic rings in benzoate derivatives, see: (a) Schweizer, W. B.; Dunitz, J. D. Helv. Chim. Acta 1982, 65, 1547-1554. (b) Bicerano, J.; Clark, H. A. Macmmolecules 1988, 21, 585-597. (c) Bicerano, J.; Clark, H. A. Macromolecules 1988, 21, 597-603. (d) Coulter, P.; Windle, A. H. Macromolecules 1989, 22, 1129-1136. (e) Emsley, J. W.; Furby, M. I. C.; de Luca, G. Liquid Crystals 1996, 21, 877-883.
96. For discussions concerning the twist between the component aromatic rings in benzoate derivatives, see: (a) Schweizer, W. B.; Dunitz, J. D. Helv. Chim. Acta 1982, 65, 1547-1554. (b) Bicerano, J.; Clark, H. A. Macmmolecules 1988, 21, 585-597. (c) Bicerano, J.; Clark, H. A. Macromolecules 1988, 21, 597-603. (d) Coulter, P.; Windle, A. H. Macromolecules 1989, 22, 1129-1136. (e) Emsley, J. W.; Furby, M. I. C.; de Luca, G. Liquid Crystals 1996, 21, 877-883.
97. For discussions concerning the twist between the component aromatic rings in benzoate derivatives, see: (a) Schweizer, W. B.; Dunitz, J. D. Helv. Chim. Acta 1982, 65, 1547-1554. (b) Bicerano, J.; Clark, H. A. Macmmolecules 1988, 21, 585-597. (c) Bicerano, J.; Clark, H. A. Macromolecules 1988, 21, 597-603. (d) Coulter, P.; Windle, A. H. Macromolecules 1989, 22, 1129-1136. (e) Emsley, J. W.; Furby, M. I. C.; de Luca, G. Liquid Crystals 1996, 21, 877-883.
98. For discussions concerning the twist between the component aromatic rings in benzoate derivatives, see: (a) Schweizer, W. B.; Dunitz, J. D. Helv. Chim. Acta 1982, 65, 1547-1554. (b) Bicerano, J.; Clark, H. A. Macmmolecules 1988, 21, 585-597. (c) Bicerano, J.; Clark, H. A. Macromolecules 1988, 21, 597-603. (d) Coulter, P.; Windle, A. H. Macromolecules 1989, 22, 1129-1136. (e) Emsley, J. W.; Furby, M. I. C.; de Luca, G. Liquid Crystals 1996, 21, 877-883.
99. For discussions concerning the twist between the component aromatic rings in benzoate derivatives, see: (a) Schweizer, W. B.; Dunitz, J. D. Helv. Chim. Acta 1982, 65, 1547-1554. (b) Bicerano, J.; Clark, H. A. Macmmolecules 1988, 21, 585-597. (c) Bicerano, J.; Clark, H. A. Macromolecules 1988, 21, 597-603. (d) Coulter, P.; Windle, A. H. Macromolecules 1989, 22, 1129-1136. (e) Emsley, J. W.; Furby, M. I. C.; de Luca, G. Liquid Crystals 1996, 21, 877-883.
100. This nematic phase has been used previously in the study of induced cholesteric phases, see: Nacari, J.; Spada, G. P.; Gottarelli, G.; Weiss, R. G. J. Am. Chem. Soc. 1987, 109, 4352-4357.
101. Smectic C host phase MX8056 from Displaytech Inc., Boulder, Colorado.
102. Significantly, the sign of the Cotton effect arising from the aromatic chromophores in the CD spectra of the polymers and induced cholesteric and smectic C liquid crystalline phases are the same, and defines their helical sense, which has been assigned M or P on the basis of comparison with previous studies of polymers and induced phases. See ref 40.
103. Iglesias, R.; Serrano, J. L.; Sierra, T. Liq. Cryst. 1997, 22, 37-46.
104. Barberá, J.; Marcos, M.; Serrano, J. L. Mol. Cryst. Liq. Cryst. 1987, 149-225.
105. (a) Goodby, J. W.; Leslie, T. M. Mol. Cryst. Liq. Cryst. 1984, 110, 175-203.
106. (b) Terashima, K.; Ichihashi, M.; Kikuchi, K.; Furukawa, K.; Inukai, T. Mol. Cryst. Liq. Cryst. 1986, 141, 237-249.
107. 1H NMR results, UV - vis spectra of the monomers at various concentrations and temperatures showed no significant differences.
108. 1H NMR results, UV - vis spectra of the monomers at various concentrations and temperatures showed no significant differences.
109. 1H NMR results, UV - vis spectra of the monomers at various concentrations and temperatures showed no significant differences.
110. 1H NMR results, UV - vis spectra of the monomers at various concentrations and temperatures showed no significant differences.
111. (a) Ramos, E. Ph.D. Thesis, Universitat Autonoma de Barcelona, Spain, 1996.
112. Selection of the 14 solvents, representative of the most relevant solute-solvent interactions, was made on the basis of solvent classification guidlines. See: (b) Ventosa, N. Ph.D. Thesis, Universitat Ramon Llull, Spain, 1997. (c) Ventosa, N.; Ruiz-Molina, D.; Rovira, C.; Tomás, X.; André, J.-J.; Veciana, J. Manuscript in preparation.
113. Selection of the 14 solvents, representative of the most relevant solute-solvent interactions, was made on the basis of solvent classification guidlines. See: (b) Ventosa, N. Ph.D. Thesis, Universitat Ramon Llull, Spain, 1997. (c) Ventosa, N.; Ruiz-Molina, D.; Rovira, C.; Tomás, X.; André, J.-J.; Veciana, J. Manuscript in preparation.
114. As far as we are aware, only King and Borodinsky (ref 11c) have performed a limited study of the effects of solvent on the polymerization of achiral isocyanides.
115. Taft, R. W.; Abboud, J.-L. M.; Kamlet, M. J.; Abraham, M. H. J. Soln. Chem. 1985, 14, 153-186.
116. Hildebrand, J. H.; Scott, R. L. The Solubility of Non-Electrolytes, 3rd ed.; Dover Publications: New York, 1964.
117. For two recent articles, see: (a) Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1997, 119, 1129-1130. (b) Linwane, P.; Magnus, N.; Magnus, P. Nature 1997, 385, 799-801. The latter example is a result of a folded conformation brought about by cation binding. For a very recent report has detailed long distance transfer of chirality in the formation of poly(isocyanide)s derived from helicenes, see: Chen, J. P.; Gao, J. P.; Wang, Z. Y. Polym. Int. 1997, 44, 83-87.
118. For two recent articles, see: (a) Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1997, 119, 1129-1130. (b) Linwane, P.; Magnus, N.; Magnus, P. Nature 1997, 385, 799-801. The latter example is a result of a folded conformation brought about by cation binding. For a very recent report has detailed long distance transfer of chirality in the formation of poly(isocyanide)s derived from helicenes, see: Chen, J. P.; Gao, J. P.; Wang, Z. Y. Polym. Int. 1997, 44, 83-87.
119. For two recent articles, see: (a) Heinemann, C.; Demuth, M. J. Am. Chem. Soc. 1997, 119, 1129-1130. (b) Linwane, P.; Magnus, N.; Magnus, P. Nature 1997, 385, 799-801. The latter example is a result of a folded conformation brought about by cation binding. For a very recent report has detailed long distance transfer of chirality in the formation of poly(isocyanide)s derived from helicenes, see: Chen, J. P.; Gao, J. P.; Wang, Z. Y. Polym. Int. 1997, 44, 83-87.
120. Odd-even effects in aliphatic chains have also been observed in amphiphilic assemblies, see: (a) Yamada, N.; Okuyama, K.; Serizawa, T.; Kawasaki, M.; Oshima, S. J. Chem. Soc., Perkin Trans. 2 1996, 2707-2713. (b) Shimizu, T.; Mitsutoshi, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
121. Odd-even effects in aliphatic chains have also been observed in amphiphilic assemblies, see: (a) Yamada, N.; Okuyama, K.; Serizawa, T.; Kawasaki, M.; Oshima, S. J. Chem. Soc., Perkin Trans. 2 1996, 2707-2713. (b) Shimizu, T.; Mitsutoshi, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
122. The influence of π-π interactions in synthesis has been discussed. For a review, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. For concrete examples, see: (b) Corey, E. J.; Decker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616-8618. (c) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35-42. (d) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157. (e) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
123. The influence of π-π interactions in synthesis has been discussed. For a review, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. For concrete examples, see: (b) Corey, E. J.; Decker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616-8618. (c) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35-42. (d) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157. (e) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
124. The influence of π-π interactions in synthesis has been discussed. For a review, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. For concrete examples, see: (b) Corey, E. J.; Decker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616-8618. (c) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35-42. (d) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157. (e) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
125. The influence of π-π interactions in synthesis has been discussed. For a review, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. For concrete examples, see: (b) Corey, E. J.; Decker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616-8618. (c) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35-42. (d) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157. (e) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
126. The influence of π-π interactions in synthesis has been discussed. For a review, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. For concrete examples, see: (b) Corey, E. J.; Decker, K. B.; Varma, R. K. J. Am. Chem. Soc. 1972, 94, 8616-8618. (c) Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35-42. (d) Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156-8157. (e) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1996, 118, 11038-11053.
127. Dipole-dipole interactions leading to helical structures induced in nematic liquid crystals has been proposed. See: Khachaturyan, A. G. J. Phys. Chem. Solids 1975, 36, 1055-1061.
128. Walba, D. M.; Stevens, F.; Clark, N. A.; Parks, D. C. Acc. Chem. Res. 1996, 29, 591-597.
129. (a) Teerenstra, M. N.; Klap, R. D.; Bijl, M. J.; Schouten, A. J.; Nolte, R. J. M., Verbiest, T., Persoons, A. Macromolecules 1996, 29, 4871-4875.
130. (b) Teerenstra, M. N.; Hagting, J. G.; Schouten, A. J.; Nolte, R. J. M.; Kauranen, M.; Verbiest, T.; Persoons, A. Macromolecules 1996, 29, 4876-4879.