Ring strain release as a strategy to enable the singlet state photodecarbonylation of crystalline 1,4-cyclobutanediones

Journal of Physical Organic Chemistry

Volumn 24, Issue 10, 2011, Pages 883-888

  Kuzmanich, Gregory ^a   Garcia Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

crystalline photochemistry; nanocrystals; oxyallyl; photochemistry; photodecarbonylation

Indexed keywords

BIRADICAL LIFETIME; BIRADICALS; CLEAVAGE REACTION; CYCLIC KETONES; HALF LIVES; LONG LIFETIME; NANOCRYSTALLINES; OXYALLYL; PHOTODECARBONYLATION; RING STRAINS; SINGLET STATE; SMALL RINGS; SOLID-STATE PHOTOCHEMISTRY; STABILIZING GROUPS; TRIPLET STATE;

CHEMICAL REACTIONS; CRYSTALS; KETONES; ORGANIC COMPOUNDS; REACTION INTERMEDIATES;

CRYSTALLINE MATERIALS;

EID: 80053328992     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1902     Document Type: Conference Paper

References (58)

1. J. R. Scheffer, Acc. Chem. Res. 1980, 13, 283.
2. M. D. Hollingsworth, J. M. McBride, Adv. Photochem. 1990, 15, 279.
3. H. Ihmels, J. R. Scheffer, Tetrahedron 1999, 55, 885.
4. H. E. Zimmerman, S. Zhu, J. Am. Chem. Soc. 1995, 117, 5245.
5. M. A. Garcia-Garibay, Acc. Chem. Res. 2003, 36, 491.
6. M. A. Garcia-Garibay, S. Shin, C. Sanrame, Tetrahedron 2000, 56, 6729.
7. J. Hallmann, W. Morgenroth, C. Paulmann, J. Davaasambuu, Q. Kong, M. Wulff, S. Techert, J. Am. Chem. Soc. 2009, 131, 15018.
8. M. A. Garcia-Garibay, Photochem. Photobiol. Sci. 2010, 9, 1574.
9. M. Bertmer, R. C. Nieuwendaal, A. B. Barnes, S. E. Hayes, J. Phys. Chem. B 2006, 110, 6270.
10. V. Ramamurthy, K. Venkatesan, Chem. Rev. 1987, 87, 433.
11. J. Sankaranarayanan, L. Bort, J. A. Krause, S. M. Mandel, P. Chen, E. E. Brooks, P. Tsang, A. D. Gudmundsdottir, Org. Lett. 2008, 10, 937.
12. J. Harada, K. Ogawa, Chem. Soc. Rev. 2009, 28, 2244.
13. S. Shiraki, M. A. Garcia-Garibay, in: Handbook of Synthetic Photochemistry (Eds:, A. Albini, M. Fagnoni,), John Wiley & Sons, Hoboken, 2010.
14. M. D. Cohen, G. M. J. Schmidt, J. Chem. Soc. 1964, 53, 1996.
15. M. D. Cohen, G. M. J. Schmidt, F. I. Sonntag, J. Chem. Soc. 1964, 53, 2000.
16. G. M. J. Schmidt, J. Chem. Soc. 1964, 53, 2014.
17. L. M. Campos, M. A. Garcia-Garibay, in: Reviews of Reactive Intermediate Chemistry (Eds:, M. S. Platz, M. Jones, R. Moss,), John Wiley & Sons, Hoboken, 2007.
18. L. M. Campos, D. Ng, Z. Yang, H. Dang, H. L. Martinez, M. A. Garcia-Garibay, J. Org. Chem. 2002, 67, 3749.
19. G. Kuzmanich, A. Natarajan, K. K. Chin, M. Veerman, C. J. Mortko, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2008, 130, 1140.
20. G. Kuzmanich, M. N. Gard, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2009, 131, 11606.
21. D. Weiss, in: Organic Photochemistry, Vol. 5, (Ed.:, A. Padwa,), Marcel Deker: New York, 1981, 347.
22. E. W.-G. Diau, C. Kötting, T. I. Sølling, A. H. Zewail, Chem. Phys. Chem. 2002, 3, 57.
23. G. Kuzmanich, F. Spänig, C.-K. Tsai, J. M. Um, R. M. Hoekstra, K. N. Houk, D. M. Guldi, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2001, ASAP.
24. B. A. Hess, Jr, L. Smentek, A. R. Brash, J. K. Cha, J. Am. Chem. Soc. 1999, 121, 5603.
25. A. R. Brash, S. W. Baertschi, C. D. Ingram, T. M. Harris, Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 3382.
26. R. Kolijak, O. Boutaud, B.-H. Shieh, N. Samel, A. R. Brash, Science 1997, 277, 1994.
27. R. Lee, C. H. Yoon, J. Chem. Soc. Chem. Commun. 1994, 479.
28. T. Noriko, S. Yamazaki, Y. Shinichi, Org. Biomol. Chem. 2008, 6, 3109.
29. G. D. Hamblin, R. P. Jimenez, T. S. Sorensen, J. Org. Chem. 2007, 72, 9439.
30. A. R. Matlin, P. M. Lahti, D. Appella, A. Straumanic, S. Lin, H. Patel, K. P. Schrieber, J. Pauls, P. Paulerson, J. Am. Chem. Soc. 1999, 121, 2164.
31. G. Liang, D. Trauner, J. Am. Chem. Soc. 2004, 126, 9544.
32. J. Hauang, A. J. Frontier, J. Am. Chem. Soc. 2007, 129, 8060.
33. W. He, I. R. Herrick, T. A. Atesin, P. A. Caruana, C. A. Kellenberger, A. J. Frontier, J. Am. Chem. Soc. 2008, 130, 1003.
34. B. Foehlisch, I. Herrscher, Chem. Ber. 1986, 119, 524.
35. S. Bhargava, J. Hou, M. Parvez, T. S. Sorensen, J. Am. Chem. Soc. 2005, 127, 3704.
36. A. G. Moiseev, M. Abe, E. O. Danilov, D. C. Neckers, J. Org. Chem. 2007, 72, 2777.
37. H. E. Zimmerman, V. Suryanarayan, Eur. J. Org. Chem. 2007, 24, 4091.
38. I. Gomez, S. Olivella, M. Reguero, A. Riera, A. Sol, J. Am. Chem. Soc. 2002, 124, 15375.
39. W. K. Chung, S. K. Lam, B. Lo, L. L. Lui, W.-T. Wong, P. Chiu, J. Am. Chem. Soc. 2009, 131, 4556.
40. T. Ichino, S. M. Villano, A. J. Gianola, D. J. Goebbert, L. Velarde, A. Sanov, S. J. Blanksby, X. Zhou, D. A. Hrovat, W. T. Borden, W. C. Lineberger, Angew. Chem. Int. Ed. 2009, 48, 8509.
41. D. Lim, D. A. Hrovat, W. T. Borden, W. L. Jorgensen, J. Am. Chem. Soc. 1994, 116, 3494.
42. V. Mozhayskiy, D. J. Boebbert, L. Velarde, A. Sanov, A. I. Krylov, J. Phys. Chem. A 2010, 114, 6935.
43. J. A. Hyatt, Organic Reactions, John Wiley & Sons, Hoboken, 1994.
44. H. Kasai, H. S. Nalwa, H. Oikawa, S. Okada, H. Matsuda, N. Minami, A. Kakuta, K. Ono, A. Mukoh, H. Nakanishi, Jpn. J. Appl. Phys. 1992, 31, 1132.
45. J. J. Kuhn, S. E. Braslavsky, R. Schmidt, Pure Appl. Chem. 2004, 76, 2105.
46. N. J. Turro, P. A. leermakers, H. R. Wilson, D. C. Neckers, G. W. Byers, G. F. Vesley, J. Am. Chem. Soc. 1965, 87.
47. A. P. Krapcho, B. Abegaz, J. Org. Chem. 1974, 39, 2251.
48. J. L. E. Erickson, F. E. Collins, Jr., B. L. Owen, J. Org. Chem. 1966, 31, 480.
49. J. D. Dunitz, J. Bernstein Accounts of Chemical Research 1995 28 (4), 193-200
50. F. W. McLaffery, Wiley Registry of Mass Spectral Data, Vol. 9, John Wiley & Sons Inc., Hoboken, 2009.
51. K. Kumura, M. Takamura, S. Koshibe, M. Juro, Y. Fukuda, Y. Odaira, Bull. Chem. Soc. Jpn. 1976, 49, 741.
52. S. L. Murov, I. Carmichael, G. L. Hug, Handbook of Photochemistry, 2nd edn, Marcel Dekker, Inc., New York, 1993.
53. M. Veerman, M. J. E. Resendiz, M. A. Garcia-Garibay, Org. Lett. 2006, 8, 2615.
54. Generation of 2 by irradiation of dione 1 in neat furan gave both alkene 4 (95%) and 5 (5%). Examples involving sterically hindered oxyally have shown that it is generally not isolatable:, F. D. Greene, D. B. Sclove, J. F. Pazos, R. L. Camp, J. Am. Chem. Soc. 1970, 92, 7488.
55. Generation of 2 by irradiation of dione 1 in neat furan gave both alkene 4 (95%) and 5 (5%). Examples involving sterically hindered oxyally have shown that it is generally not isolatable:, M. H. J. Cordes, J. A. Berson, J. Am. Chem. Soc. 1996, 118, 6241.
56. Packing coefficients were defined by Kitaigorodskii as the volume of molecules in the unit cell relative to the total volume of the unit cell., A. I. Kitaigorodski, Molecular Crystals and Molecules, Academic Press, New York, 1973.
57. T. Choi, D. Cizmeciyan, S. I. Kahn, M. A. Garcia-Garibay, J. Am. Chem. Soc. 1995, 117, 12893.
58. W. W. Wright, J. C. Baez, J. M. Vanderkooi, Anal. Biochem. 2002, 307, 167.