Solid state photochemistry: Absolute asymmetric photocyclization of an achiral S-aryl o-benzoylbenzothioate to an optically active phthalide involving a novel phenyl migration

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8138-8139

  Sakamoto, Masami ^a   Takahashi, Masaki ^a   Moriizumi, Shin ^a   Yamaguchi, Kentaro ^a   Fujita, Tsutomu ^a   Watanabe, Shoji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHTHALIDE DERIVATIVE;

ARTICLE; CIRCULAR DICHROISM; CRYSTALLOGRAPHY; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0029814110     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960823h     Document Type: Article

References (20)

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2. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433-481.
3. Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991, pp 185-246.
4. Zimmerman, H. E.; Zhu, Z. J. Am. Chem. Soc: 1995, 117, 5245-5262.
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7. Evans, S. V.; Garcia-Garibay, M.; Omkaram, N.; Scheffer, J. R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1986, 108, 5648-5649.
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9. Roughton, A. L.; Muneer, M.; Demuth, M. J. Am. Chem. Soc. 1993, 115, 2085-2086.
10. Sakamoto, M.; Hokari, N.; Takahashi, M.; Fujita, T.; Watanabe, S.; Iida, I.; Nishio, T. J. Am. Chem. Soc. 1993, 115, 818.
11. Toda, F.; Tanaka, K. Supramol. Chem. 1994, 3, 87-88.
12. Sakamoto, M.; Takahashi, M.; Shimizu, M.; Fujita, T.; Nishio, T.; Iida, I.; Yamaguchi, K.; Watanabe, S. J. Org. Chem. 1995, 60, 7088-7089.
13. Recently we reported that photolysis of a thioester chromophore substituted on the nitrogen atom of α-oxoamide gave oxazolidinedione via a radical pair intermediate: Sakamoto, M.; Takahashi, M.; Fujita, T.; Watanabe, S.; Iida, I.; Nishio, T. J. Org. Chem. 1995, 60, 3476-3477.
14. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB IEZ, U.K.
15. 2 are torsion angles C1-C2-C15-C16 and O1-C15-C2-C3, respectively, for the twist angle of C15(=O1)-C16. The twist angle τ for C7(=O2)-S1 is determined in the same manner.
16. -1. The structure was solved by the direct method and refined by the method of full-matrix least squares. The absolute configuration was solved by the Bijvoet difference method. For 2403 Friedel pairs. 1736 showed agreement and 667 showed disagreement between observed and calculated ΔF for the structure of molecules with (R)-configuration, which clearly showed that this structure, given in Figure 3, is that with the correct absolute configuration. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB IEZ, U.K.
17. Penn, J. H.; Liu, F. J. Org. Chem. 1994, 59, 2608-2612.
18. Crich, D.; Chen, C.; Hwang, J. T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc: 1994, 116, 8937-8951.
19. Intermolecular addition of an o-tolylthio group is also excluded because there is no interatomic sulfur atom within 5.3 A from the benzoyl carbon atom.
20. In order to exclude the involvement of path A. we also analyzed an S-phenyl 2-benzoyl-4-methylbenzothioate. With a methyl group para to the thioester. this compound allows for unambiguous identification of products from phenyl or phenylthio group migration. The formation of only one phthalide (6-methyl-3-phenyl-3-phenylthiophthalide) involving phenyl migration (path B) was observed both in solution and in the solid state.