Photoreactions of substituted o-cresyl acylates in cyclohexane and in polyethylene films. the influences of intra- and inter-molecular 'crowding' effects

Photochemical and Photobiological Sciences

Volumn 8, Issue 7, 2009, Pages 916-925

  Chen, Yu Zhe ^a   Weiss, Richard G ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(2 HYDROXYPHENYL)DIPHENYLMETHANOL; 1 (3 BENZHYDRYL 2 HYDROXYPHENYL)ETHANONE; 1 (3 BENZYL 2 HYDROXYPHENYL)ETHANONE; 1 (3 BENZYL 4 HYDROXYPHENYL)ETHANONE; 2 BENZHYDRYLPHENOL; 2 BENZHYDRYLPHENYL ACETATE; 2 BENZYHYDRYLPHENYL OCTANOATE; 2 BENZYLPHENYL ACETATE; 2 CRESYL ACETATE; 2 HYDROXY 3 METHYLACETOPHENONE; CYCLOHEXANE; ESTER DERIVATIVE; POLYETHYLENE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTALLIZATION; FILM; IRRADIATION; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS;

EID: 68149149714     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b902109d     Document Type: Article

References (60)

1. J. D. Coyle Photochemistry of carboxylic acid derivatives Chem. Rev. 1978 78 97 123
2. D. Bellus Photo-Fries rearrangement and related photochemical [1, j]-shifts (j = 3, 5, 7) of carbonyl and sulfonyl groups Adv. Photochem. 1971 8 109 159
3. M. A. Miranda, CRC Handbook of Organic Photochemistry and Photobiology, ed., W. M. Horspool, and, P. S. Song., CRC Press LLC, Boca Raton, 1995, Ch. 47
4. N. P. Gritsan Y. P. Tsentalovich A. V. Yurkovskaya R. Z. Sagdeev Laser Flash Photolysis and CIDNP Studies of 1-Naphthyl Acetate Photo-Fries Rearrangement J. Phys. Chem. 1996 100 4448 4458
5. W. Adam Multiplicity of the photo-Fries rearrangement J. Chem. Soc., Chem. Commun. 1974 289 290
6. W. Adam J. Arce de Sanabia CIDNP [chemically induced dynamic nuclear polarization] evidence for radical pair mechanism in photo-Fries rearrangement J. Org. Chem. 1973 38 2571 2572
7. J. W. Meyer G. S. Hammond Mechanism of photochemical reactions in solution. LXX. Photolysis, of aryl esters J. Am. Chem. Soc. 1972 94 2219 2228
8. H. Shizuka T. Morita Photochemical rearrangement of phenyl acetate Bull. Chem. Soc. Jpn. 1969 42 1831 1836
9. R. Suau G. Torres M. Valpuesta The photo-Fries rearrangement of 2,5-disubstituted phenyl acetates Tetrahedron Lett. 1995 36 1311 1314
10. R. A. Finnegan D. Knutson Additional examples of a novel photo-decarboxylation process; the preparation of some hindered aryl ketones Chem. Ind. 1965 1837 1838
11. R. A. Finnegan D. Knutson Photochemical studies. VII. Solvent, effects on the photolysis of aryl esters: Fries rearrangement vs. decarboxylation Tetrahedron Lett. 1968 9 3429 3432
12. R. A. Finnegan D. Knutson Stereochemistry of photodecarboxylation and photodecarbonylation reactions of aryl esters. The photolysis of (S)-(+)-3, 5-di-tert-butylphenyl 2-methylbutanoate J. Am. Chem. Soc. 1967 89 1970 1972
13. T. Mori R. G. Weiss Y. Inoue Enhanced photodecarboxylation of an aryl ester in polyethylene films Org. Lett. 2003 5 4661 4664
14. T. Mori R. G. Weiss Y. Inoue Mediation of conformationally controlled photodecarboxylations of chiral and cyclic aryl esters by substrate structure, temperature, pressure, and medium constraints J. Am. Chem. Soc. 2004 126 8961 8975
15. C. Cui R. G. Weiss 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. 1993 115 9820 9821
16. W. Gu A. J. Hill X. Wang C. Cui R. G. Weiss Photorearrangements of five 1- and 2-naphthyl acylates in three unstretched and stretched polyethylene Films. Does reaction selectivity correlate with free volumes measured by positron annihilation lifetime spectroscopy? Macromolecules 2000 33 7801 7811
17. W. Gu M. Warrier B. Schoon V. Ramamurthy R. G. Weiss Understanding the influence of active (zeolite) and passive (polyethylene) reaction cages on photo-Claisen rearrangements of aryl benzyl ethers Langmuir 2000 16 6977 6981
18. C. Luo P. Passin R. G. Weiss Comparisons of photo-Fries rearrangements of 4-dodecylphenyl phenylacetate and two structurally related esters in hexane and polyethylene cages. How important are anchoring chains? Photochem. Photobiol. 2006 82 163 170
19. W. Gu R. G. Weiss Mediation of photochemical reactions of 1-naphthyl phenylacylates by polyolefin films. A 'radical clock' to measure rates of radical-pair cage recombinations in 'viscous space' Tetrahedron 2000 56 6913 6925
20. W. Gu M. Warrier V. Ramammurthy R. G. Weiss Photo-Fries reactions of 1-naphthyl esters in cation-exchanged zeolite Y and polyethylene media J. Am. Chem. Soc. 1999 121 9467 9468
21. U. Bhattacharjee C. A. Chesta R. G. Weiss Temperature-dependent cage effects from triplet radical pairs generated upon irradiation of 1-(4-methylphenyl)-3-phenyl-2-propanone in polyethylene films Photochem. Photobiol. Sci. 2004 3 287 295
22. C. A. Chesta J. Mohanty W. M. Nau U. Bhattacharjee R. G. Weiss New insights into the mechanism of triplet radical-pair combinations. The persistent radical effect masks the distinction between in-cage and out-of-cage processes J. Am. Chem. Soc. 2007 129 5012 5022
23. J. Xu R. G. Weiss Analyses of in-cage singlet radical-pair motions from irradiations of 1-naphthyl (R)-1-phenylethyl ether and 1-naphthyl (R)-2-phenylpropanoate in n-alkanes J. Org. Chem. 2005 70 1243 1252
24. J. Xu R. G. Weiss Enantioselectivity of prochiral radical-pair recombinations. Reaction cavity differentiation in polyethylene films Org. Lett. 2003 5 3077 3080
25. J. Xu R. G. Weiss Combinations of chiral and prochiral singlet radical-pairs in reaction cavities of polyethylene films. Control and analysis of radical tumbling and translation Photochem. Photobiol. Sci. 2005 4 348 358
26. W. Gu S. Bi R. G. Weiss Photo-Fries rearrangements of 1-naphthyl esters in the glassy and melted states of poly(vinyl acetate). Comparisons with reactions in less polar polymers and low-viscosity solvents Photochem. Photobiol. Sci. 2002 1 52 59
27. R. G. Weiss V. Ramamurthy G. S. Hammond Photochemistry in organized and confining media: a model Acc. Chem. Res. 1993 26 530 536
28. W. Brandt, and, A. Dupasquier., Eds.; Positron Solid-State Physics, North-Holland: Amsterdam, 1983
29. D. M. Schrader., and, Y. C. Jean., Eds.; Positron and Positronium Chemistry, Elsevier, Amsterdam, 1988
30. Y. C. Jean H. Nakanishi L. Y. Hao T. C. Sandreczki Anisotropy of free-volume-hole dimensions in polymers probed by positron-annihilation spectroscopy Phys. Rev. B: Condens. Matter Mater. Phys. 1990 42 9705 9708
31. Y. C. Jean Y. Rhee Y. Lou D. Shelby G. L. Wilkers Anisotropy of hole structures in oriented polycarbonate probed by two-dimensional angular correlation of annihilation radiation J. Polym. Sci., Part B: Polym. Phys. 1996 34 2979 2985 (Pubitemid 126556550)
32. O. E. Zimerman C. Cui X. Wang T. D. Atvars R. G. Weiss Structural characterization of five polyethylene films and the diffusion of N, N- dimethylaniline within them. Attempted correlations between probe dynamics and pertinent macroscopic and microscopic polymer properties Polymer 1998 39 1177 1185
33. C. Wang J. Xu R. G. Weiss Factors influencing orientations of covalently-attached and doped aromatic groups in stretched polyethylene films J. Phys. Chem. B 2003 107 7015 7025
34. C. Luo T. D. Z. Atvars P. Meakin A. J. Hill R. G. Weiss Determination of initial and long-term microstructure changes in ultrahigh molecular weight polyethylene induced by drawing neat and pyrenyl modified films J. Am. Chem. Soc. 2003 125 11879 11892
35. R. O. Rahn Potassium iodide as a chemical actinometer for 254 nm radiation: use of iodate as an electron scavenger Photochem. Photobiol. 1997 66 450 455
36. R. O. Rahn M. I. Stefan J. R. Bolton E. Goren P. S. Shaw K. R. Lykke Quantum yield of the iodide-iodate chemical actinometer: Dependence on wavelength and concentration Photochem. Photobiol. 2003 78 146 152
37. J. J. Talley I. A. Evans Reaction of lithium o-lithiophenoxide with carbonyl compounds J. Org. Chem. 1984 49 5267 5269
38. G. N. Dorofeenko S. M. Lukyanov L. N. Etmetchenko Synthesis and certain properties of 1, 3-benzodioxanium salts Zh. Org. Khim. 1976 12 2228 2233
39. H. Naeimi L. Morida Microwave-assisted direct ortho-acylation of phenol and naphthol derivatives by BF3(C2H5)2O Bull. Chem. Soc. Jpn. 2005 78 284 287
40. J. S. Bradshaw E. L. Loveridge L. White Photorearrangements of 2,4-disubstituted phenyl esters J. Org. Chem. 1968 33 4127 4132
41. R. D. Burkhart R. F. Boynton J. C. Merrill Diffusion and diffusion-controlled reactions involving alkyl radicals in solution J. Am. Chem. Soc. 1971 93 5013 5017
42. E. Paul R. M. Mazo Calculations of the diffusion coefficients of n-alkanes J. Chem. Phys. 1968 48 1405 1407
43. A. H. Alwattar, M. D. Lumb, and J. B. Birks, In Organic Molecular Photophysics, Eds., J. B. Birks., Wiley, New York, 1973, vol. 1, p. 403
44. R. Nakagaki M. Hiramatsu T. Watanabe Y. Tanimoto S. Nagakura Magnetic isotope and external magnetic field effects upon the photo-Fries rearrangement of 1-naphthyl acetate J. Phys. Chem. 1985 89 3222 3226
45. A. H. Alwattar, M. D. Lumb, and J. B. Birks, in Organic Molecular Photophysics, Eds., J. B. Birk., Wiley, New York, 1973, vol. 1, p 403
46. C. Cui X. Wang R. G. Weiss Investigation of the photo-Fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. Comparison with the acid-catalyzed reactions J. Org. Chem. 1996 61 1962 1974
47. V. Ramamurthy., Ed. Photochemistry in Organized and Constrained Media VCH, New York, 1991
48. H. E. Zimmerman I. V. Alabugin W. Chen Z. Zhu Dramatic effects of crystal morphology on solid state reaction course; Control by crystal disorder; mechanistic and exploratory organic photochemistry J. Am. Chem. Soc. 1999 121 11930 11931
49. D. E. Axelson G. C. Levy L. Mandelkern A quantitative analysis of low-density (branched) polyethylenes by carbon-13 Fourier transform nuclear magnetic resonance at 67.9 MHz Macromolecules 1979 12 41 52
50. R. P. Quirk, and M. A. A. Alsamarraie, In Polymer Handbook., J. Brandrup., E. H. Immergut., Eds.; Wiley, New York, 1989 p V/15
51. D. W. Hadley, In Structure and Properties of Oriented Polymers., I. M. Ward., Ed.; Wiley, London, 1975; Ch. 9
52. W. Glenz A. J. Peterlin Infrared studies of highly drawn linear polyethylene J. Macromol. Sci., Phys. 1970 4 473 489
53. P. J. Phillips Mechanism of orientation of aromatic molecules by stretched polyethylene Chem. Rev. 1990 90 425 436
54. Y. T. Jang P. J. Phillips E. W. Thulstrup Some comments on the mechanism of orientation of organic solutes in stretched polyethylene Chem. Phys. Lett. 1982 93 66 73
55. E. Meirovitch ESR observations on stretching-induced molecular mobility and partitioning among sites in polyethylene films J. Phys. Chem. 1984 88 2629 2635
56. J. Naciri R. G. Weiss New methods for the determination of dopant site distributions and dopant rates of diffusion in polymer films: emission from pyrenyl groups covalently attached to low-density polyethylene Macromolecules 1989 22 3928 3936
57. Z. He G. S. Hammond R. G. Weiss New methods for the determination of dopant site distributions and dopant rates of diffusion in low-density polyethylene films with covalently attached anthryl groups: fluorescence quenching by N, N-dimethylaniline in unstretched, stretched, and swelled films Macromolecules 1992 25 1568 1575
58. R. M. Jenkins G. S. Hammond R. G. Weiss Dopant site sizes and dopant rates of diffusion in low-density polyethylene films with covalently attached pyrenyl groups: fluorescence quenching by a homologous series of N, N-dialkylanilines in unstretched and stretched films J. Phys. Chem. 1992 96 496 502
59. J. Konwerska-Hrabowska The power of spectroscopic methods in the determination of the relative orientation of guest molecules in a stretched polyethylene (PE) matrix Appl. Spectrosc. 1985 39 976 979
60. J. Michl, in Spectroscopy with polarized light: solute alignment by photoselection, in liquid crystals, polymers, and membranes., J. Michl., and, E. W. Thulstrup., Eds, Deerfield Beach, FL, USA, VCH, 1986, Ch. 3