Investigations of cylindrical reaction cavities from ordered phases of alkyl alkanoates and their influence on some Norrish-Yang and photo-fries reactions

Photochemistry and Photobiology

Volumn 63, Issue 6, 1996, Pages 726-734

  Baldvins, Jon E ^a   Cui, Changxing ^a   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001575601     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1996.tb09622.x     Document Type: Conference Paper

References (48)

1. Weiss, R. G. (1988) Thermotropic liquid crystals as reaction media for mechanistic investigations. Tetrahedron 44, 3413-3475.
2. Weiss, R. G., V. Ramamurthy and G S. Hammond (1993) Photochemistry in organized and confining media. Acc. Chem. Res. 23, 530-536.
3. Ramamurthy, V., R. G. Weiss and G. S. Hammond (1993) A model for the influence of organized media on photochemical reactions. In Advances in Photochemistry, Vol. 18 (Edited by D. H. Volman, G. S. Hammond and D. C. Neckers), pp. 67-234. Wiley-Interscience, New York.
4. Weiss, R. G. (1991) Photochemical processes in liquid crystals. In Photochemistry in Organized and Constrained Media (Edited by V. Ramamurthy), pp. 603-690. VCH Publishers. New York.
5. Weiss, R. G., R. L. Treanor and A. Nunez (1988) Norrish II reactions of rod-like ketones in ordered media comprised of rod-like layered solvent molecules. Pure Appl. Chem. 60, 999-1008.
6. He, Z. and R. G. Weiss (1990) Length and direction-specific solute-solvent interactions as determined from Norrish II reactions of p-alkyl alkylphenones in ordered phases of n-butyl stearate. J. Am. Chem. Soc. 112, 5535-5541.
7. Treanor, R. L. and R. G. Weiss (1987) Liquid-crystalline solvents as mechanistic probes. 23. Norrish II reactions of 2- and sym-alkanones in the isotropic, smectic B, and crystalline phases of n-butyl stearate. Tetrahedron 43, 1371-1391.
8. Ramesh, V. and R. G. Weiss (1986) Liquid-crystalline solvents as mechanistic probes. 20. Crystalline and smectic B solvent control over the selectivity of photodimerization of n-alkyl cinnamates. J. Org. Chem. 51, 2535-2539.
9. Dryden, J. S. (1957) Dielectric absorption and phase changes in an aliphatic ester in the waxy form. J. Chem. Phys. 26, 604-607.
10. Krishnamurti, D., K. S. Krishnamurthy and R. Shashidhar (1969) Thermal, optical, x-ray, infrared, and NMR studies on the α-phase of some saturated aliphatic esters. Mol. Cryst. Liq. Cryst. 8, 339-366.
11. Krishnamurthy, K. S. and D. Krishnamurti (1970) Proton magnetic resonance absorption in n-butyl stearate. Mol. Cryst. Liq. Cryst. 6, 407-413.
12. Krishnamurthy, K. S. (1988) Optical microscopic study of n-propyl and n-butyl stearates in their α-phase. Mol. Cryst. Liq. Cryst. 132, 255-263.
13. Weiss, R. G. (1996) Creation of liquid crystalline phases. A comparative view emphasizing structure and shape of mononer liquid crystals. In Polymer Liquid Crystals. Thermophysical and Mechanical Properties, Vol. 3 (Edited by W. Brostow). Chapman and Hall, London. (In press)
14. Wagner, P. J., P. A. Kelso and R. G. Zepp (1972) Type II photoprocesses of phenyl ketones. Evidence for a biradical intermediate. J. Am. Chem. Soc. 94, 7480-7488.
15. Wagner, P. J., P. A. Kelso, A. E. Kemppainen, J. M. McGrath, H. N. Schott and R. G. Zepp (1972) Type II photoprocesses of phenyl ketones. Glimpse at the behavior of 1,4 biradicals. J. Am. Chem. Soc. 94, 7506-7512.
16. Wagner, P. J. (1967) Solvent effects on type II photoelimination of phenyl ketones. J. Am. Chem. Soc. 89, 5898-5901.
17. Wagner, P. J. (1971) Type II photoelimination and photocyclization of ketones. Acc. Chem. Res. 4, 168-177.
18. Wagner, P. J. (1995) Norrish type II photoelimination of ketones: cleavage of 1,4-biradicals formed by γ-hydrogen abstraction. In Organic Photochemistry and Photobiology (Edited by W. M. Horspool and P.-S. Song), pp. 449-470. CRC Press, Boca Raton, FL.
19. Weiss, R. G. (1995) Norrish type II processes of ketones: influence of environment. In Organic Photochemistry and Photobiology (Edited by W. M. Horspool and P.-S. Song), pp. 471-483. CRC Press, Boca Raton, FL.
20. Yang, N. C. and D.-D. H. Yang (1958) Photochemical reactions of ketones in solution. J. Am. Chem. Soc. 80, 2913-2914.
21. Yang, N. C. and S. P. Elliott (1968) Reactivity of the n, π* singlet state of 2-hexanone. J. Am. Chem. Soc. 90, 4194-4195.
22. Cohen, M D. (1975) Photochemistry of organic solids. Angew. Chem. 87, 439-447.
23. Bellus, D. (1971) Photo-Fries rearrangement and related photochemical [1,j]-shifts (j = 3, 5, 7) of carbonyl and sulfonyl groups. In Advances in Photochemistry, Vol. 8 (Edited by J. N. Pitts, Jr., G. S. Hammond and W. A. Noyes, Jr.), pp. 109-159. Wiley, New York.
24. Meyer, J. W. and G. S. Hammond (1970) Vapor phase photolysis of phenyl acetate. J. Am. Chem. Soc. 94, 2187-2189.
25. Cui, C., X. Wang and R. G. Weiss (1995) Investigation of the photo-Fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. J. Org. Chem. (In press)
26. Cui, C. and R. G. Weiss (1993) Photo-Fries rearrangements of 2-naphthyl acylates as probes of the size and shape of guest sites afforded by unstretched and stretched low-density polyethylene films. A case of remarkable selectivity. J. Am. Chem. Soc. 115, 9820-9821
27. Cui, C. (1995) Factors controlling the photo-fries rearrangements of 2-naphthyl acylates in polyethylene films. Ph.D. Thesis, Georgetown University, Washington, DC.
28. He, Z. (1991) Part 1: New methods to study the properties of unstretched, stretched and swelled polyethylene films with covalently attached anthryl groups. Part 2: Site and direction specific solute-solvent interactions of rod-like hydroxy-1,4-biradicals in the layered matrices of n-butyl stearate. Ph.D. Thesis, Georgetown University, Washington, DC.
29. Nerbonne, J. and R. G. Weiss (1979) Liquid crystalline solvents as mechanistic probes. III. The influence of ordered media on the efficiency of the photodimerization of acenaphthylene. J. Am. Chem. Soc. 101, 402-407.
30. Gray, G. W. and J. W. G. Goodby (1984) Smectic Liquid Crystals. Textures and Structures. Leonard Hill, Glasgow.
31. Moncton, D. E. and R. Pindak (1979) Long-range order in two-and three-dimensional smectic-B liquid-crystal films. Phys. Rev. Lett. 43, 701-704.
32. Leadbetter, A. J., M. A. Mazid, B. A. Kelley, J. Goodby and G. W. Gray (1979) Structure of the smectic-B phase and the nature of the smectic-B to -H transition in the N-(4-n-alkoxybenzylidene)-4′-alkylanilines. Phys. Rev. Len. 43, 630-633.
33. Belcher, A., G. Epple, I. Kuederling and A. B. Smith III (1988) Volatile components of scent material from cotton-top tamarin (Saguinus oedipus oedipus): a chemical and behavior study. J. Chem. Ecol. 14, 1367-1384.
34. Golob, N. F., R. G. Yarger and A. B. Smith III (1979) Primate chemical communication. III. Synthesis of the major volatile constituents of the marmoset (Saguinus fuscicollis) scent mark. J. Chem. Ecol. 5, 543-555.
35. Tengo, J. and G. Bergstrom (1977) Cleptoparasitism and odor mimetism in bees: do Nomada males imitate the odor of Andrena females? Science 196, 1117-1119.
36. Grula, J. W., J. D. McChesney and O. R. Taylor, Jr. (1980) Aphrodisiac pheromones of the sulfur butterflies Colias eurytheme and C. philodice (Lepidoptera, Pieridae). J. Chem. Ecol. 6, 241-256.
37. Demus, D., H. Demus and H. Zaschke (1974) Flussige Kristalle in Tabellen. Deutscher Verlag Fur Grundstoffindustrie, Berlin.
38. Demus, D. and H. Zaschke (1984) Flussige Kristalle in Tabellen II. Deutscher Verlag fur Grundstoffindustrie, Berlin.
39. Maroncelli, M., S. P. Qi, H. L. Strauss and R. G. Snyder (1982) Nonplanar conformers and the phase behavior of solid n-alkanes. J. Am. Chem. Soc. 104, 6237-6247.
40. Maroncelli, M., H. L. Strauss and R. G. Snyder (1985) The distribution of conformational disorder in the high-temperature phases of the crystalline n-alkanes. J. Chem. Phys. 82, 2811-2824.
41. Brown, M. S., D. M. Grant, W. J. Horton, C. L. Mayne and G. T. Evans (1985) Rotational dynamics of flexible alkanes. An NMR coupled relaxation and a Brownian dynamics study. J. Am. Chem. Soc. 107, 6698-6707.
42. Sauers, R. R. and L. A. Edberg (1994) Modelling Norrish type II reactions by semiempirical and ab initio methodology. J. Org. Chem. 59, 7061-7066.
43. Scheffer, J. R., M. Garcia-Garibay and D. Nalamasu (1987) The influence of the molecular crystalline environment on organic photorearrangements. Org. Photochem. 8, 249-347.
44. Scaiano, J. C. (1982) Laser flash photolysis studies of the reactions of some 1,4-biradicals. Acc. Chem. Res. 15, 252-258.
45. Morita, A. and S. Kato (1993) Theoretical study on the intersystem crossing mechanism of a diradical in the Norrish type II reaction in solution. J. Phys. Chem. 97, 3298-3313.
46. Scaiano, J. S. (1982) Does intersystem crossing in triplet biradicals generate singlets with conformational memory? Tetrahedron 38, 819-824.
47. Wang, Z., D. A. Holden and F. R. McCourt (1990) Generation of non-random chromophore distributions by the photo-Fries reactions of 2-naphthyl acetate in poly(methyl methacrylate). Macromolecules 23, 3773-3779.
48. 36 range J. Am. Chem. Soc 77, 2017-2019.