Photocyclization of 2-vinyldiphenylacetylenes and behavior of the isonaphthalene intermediates

Photochemical and Photobiological Sciences

Volumn 4, Issue 8, 2005, Pages 629-636

  Sajimon, Meledathu C ^a   Lewis, Frederick D ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 VINYLDIPHENYLACETYLENE; ACETYLENE DERIVATIVE; ISONAPHTHALENE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ELECTRONICS; FLUORESCENCE; ISOMERIZATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 23844544416     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b504997k     Document Type: Article

References (44)

1. Y. Hirata Photophysical and photochemical primary processes of diphenylacetylene derivatives and related compounds in liquid phase Bull. Chem. Soc. Jpn. 1999 72 1647-1664.
2. Y. Hirata T. Okada N. Mataga T. Nomoto Picosecond time-resolved absorption spectrum measurements of the higher excited singlet state of diphenylacetylene in the solution phase J. Phys. Chem. 1992 96 6559-6563.
3. C. Ferrante U. Kensy B. Dick Does diphenylacetylene (tolan) fluoresce from its second excited singlet state? Semiempirical MO calculations and fluorescence quantum yield measurements J. Phys. Chem. 1993 97 13457-13463.
4. D. R. Borst S. G. Chou D. W. Pratt Identification of the light-absorbing states in tolane with potential relevance to self-similar phenylacetylene dendrimers Chem. Phys. Lett. 2001 343 289-295.
5. M. Z. Zgierski E. C. Lim Nature of the ‘dark’ state in diphenylacetylene and related molecules: state switch from the linear π,π* state to the bent σ,π* state Chem. Phys. Lett. 2004 387 352-355.
6. Y. Amatatsu M. Hosokawa Theoretical study on the photochemical behavior of diphenylacetylene in the low-lying excited states J. Phys. Chem. A 2004 108 10238-10244.
7. For more detailed descriptions of the DPA singlet state, see ref. 5 and 6.
8. J. Saltiel and Y.-P. Sun, in Photochromism, Molecules and Systems, ed. H. Durr and H. Boaus-Laurent, Elsevier, Amsterdam, 1990.
9. H. E. Zimmerman L. Craft Photochemical reaction of benzoquinone with tolan Tetrahedron Lett. 1964 2131-2136.
10. H. M. Rosenberg M. P. Serve Photocycloaddition of diphenylacetylene to 2,3-dihydropyran J. Org. Chem. 1968 33 1653-1654.
11. S. P. Pappas N. A. Portnoy Substituent effects on the photoaddition of diphenylacetylene to 1,4-naphthoquinones J. Org. Chem. 1968 33 2200-2203.
12. A. R. Kim Y. J. Mah S. S. Kim Formation of o-/p-quinomethanes and p-quinodimethanes from the photoaddition of diphenylacetylene to o-quinones Bull. Korean Chem. Soc. 1998 19 1295-1297.
13. G. Kaupp M. Stark Selectivities in the photolysis of diphenylcyclobutenes Chem. Ber. 1978 111 3608-3623.
14. T. A. Zeidan S. V. Kovalenko M. Manoharan R. J. Clark I. Ghiviriga I. V. Alabugin Triplet acetylenes as synthetic equivalents of 1,2-bicarbenes: Phantom n,π* state controls reactivity in triplet photocycloaddition J. Am. Chem. Soc. 2005 127 4270-4285.
15. P. M. op den Brouw W. H. Laarhoven Photochemistry of 2-vinyldiphenylacetylene and related compounds J. Chem. Soc., Perkin Trans. 2 1982 795-799.
16. R. P. Johnson Strained cyclic cumulenes Chem. Rev. 1989 89 1111-1124.
17. D. Rodríguez A. Navarro-Vazquez L. Castedo D. Dominguez C. Saá Cyclic allene intermediates in intramolecular dehydro Diels–Alder reactions: Labeling and theoretical cycloaromatization studies J. Org. Chem. 2003 68 1938-1946.
18. F. D. Lewis X. Zuo R. S. Kalgutkar J. M. Wagner-Brennan M. A. Miranda E. Font-Sanchis J. Perez-Prieto Temperature-dependent photochemistry of 1,3-diphenylpropenes. The di-π-methane reaction revisited J. Am. Chem. Soc. 2001 123 11883-11889.
19. F. D. Lewis X. Zuo V. Gevorgyan M. Rubin Symmetry-enforced control of photochemical reactivity in 2-vinyl-1,3-terphenyl J. Am. Chem. Soc. 2002 124 13664-13665.
20. F. D. Lewis X. Zuo Conformer-specific photoisomerization of some 2-vinylbiphenyls Photochem. Photobiol. Sci. 2003 2 1059-1066.
21. D. Yue N. C. Della R. C. Larock Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones Org. Lett. 2004 6 1581-1584.
22. A. C. Greiner C. Spyckerelle P. Albrecht Aromatic hydrocarbons from geological source-I Tetrahedron 1976 32 257-260.
23. CAChe Release 6.1, Fujitsu Limited, Miahama-Ku, Chiba City, Chiba, Japan.
24. F. D. Lewis X. Zuo Activated decay pathways for planar vs. twisted singlet phenylalkenes J. Am. Chem. Soc. 2003 125 8806-8813.
25. J. A. Saltiel A. Marinari D. W. L. Chang J. C. Mitchener E. D. Megarity Trans–cis photoisomerization of the stilbenes and a reexamination of the positional dependence of the heavy-atom effect J. Am. Chem. Soc. 1979 101 2982-2996.
26. M. C. Zerner G. H. Loew R. F. Kirchner U. T. Mueller-Westerhoff An intermediate neglect of differential overlap technique for spectroscopy of transition-metal complexes. Ferrocene J. Am. Chem. Soc. 1980 102 589-599.
27. I. V. Alabugin M. Manoharan B. Breiner F. D. Lewis Control of kinetics and thermodynamics of [1,5]-shifts by aromaticity: a view through the prism of Marcus theory J. Am. Chem. Soc. 2003 125 9329-9342.
28. M. Prall A. Krüger P. R. Schreiner H. Hopf The cyclization of parent and cyclic hexa-1,3-dien-5-ynes—a combined theoretical and experimental study Chem. Eur. J. 2001 7 4386-4394.
29. J. E. Bartmess S. S. Griffith Tautomerization energetics of benzoannelated toluenes J. Am. Chem. Soc. 1990 112 2931-2936.
30. L. T. Scott W. R. Brunsvold Double-bond isomers of aromatic compounds. 1-Methylene-1,2-dihydronaphthalene J. Org. Chem. 1979 44 641.
31. W. H. Saunders, Jr. and A. F. Cockerill, Mechanisms of Elimination Reactions, Wiley-Interscience, New York, 1973.
32. A. Rauk T. S. Sorensen C. Maerker J. W. d. M. Carneiro S. Sieber P. v. R. Schleyer Axial and equatorial 1-methyl-1-cyclohexyl cation isomers both have chair conformations but differ in C–C and C–H hyperconjugation modes J. Am. Chem. Soc. 1996 118 3761-3762.
33. I. V. Alabugin M. Manoharan Effect of double-hyperconjugation on the apparent donor ability of σ-bonds: Insights from the relative stability of δ-substituted cyclohexyl cations J. Org. Chem. 2004 69 9011-9024.
34. D. Mangion J. Kendall D. R. Arnold Photosensitized (electron-transfer) deconjugation of 1-arylcyclohexenes Org. Lett. 2001 3 45-48.
35. R. M. Duhaime D. A. Lombardo I. A. Skinner A. C. Weedon Conversion of α,β-unsaturated esters to their β,γ-unsaturated isomers by photochemical deconjugation J. Org. Chem. 1985 50 873-879.
36. J. Hofmann K. Schulz A. Altmann M. Findeisen G. Zimmermann Addition and cyclization reactions in the thermal conversion of hydrocarbons with an enyne structure. Part 5. High-temperature ring-closures of 1,3-hexadien-5-ynes to naphthalenes. Competing reactions via isoaromatics, alkenylidene carbenes, and vinyl-type radicals Liebigs Ann./Rec. 1997 2541-2548.
37. Y. Hirata T. Okada T. Namoto Higher excited singlet states of diphenylacetylene in solution phase Chem. Phys. Lett. 1993 209 397-402.
38. F. D. Lewis X. Zuo Torsional barriers for planar versus twisted singlet styrenes J. Am. Chem. Soc. 2003 125 2046-2047.
39. H. J. C. Jacobs E. Havinga The NEER princlple Adv. Photochem. 1979 11 305-376.
40. U. Mazzucato F. Momicchioli Rotational isomerism in trans-1,2-diarylethylenes Chem. Rev. 1991 91 1679-1719.
41. J. Saltiel N. Tarkalanov D. F. J. Sears Conformer-specific adiabatic cis–trans photoisomerization of cis-1-(2-naphthyl)-2-phenylethene. A striking example of the NEER principle J. Am. Chem. Soc. 1995 117 5586-5587.
42. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, New York, 1971.
43. D. R. James A. Siemiarczuk W. R. Ware Stroboscopic optical boxcar technique for the determination of fluorescence lifetimes Rev. Sci. Instrum. 1992 63 1710-1716.
44. A. R. Katritzky G. Zhang L. Xie Benzotriazole-assisted aromatic ring annulation: Efficient and general syntheses of polysubstituted naphthalenes and phenanthrenes J. Org. Chem. 1997 62 721-725.