Synthesis, structure, and photochemistry of tetrakis(trimethylsilyl)-p-benzoquinone

Chemistry Letters

Volumn , Issue 3, 2000, Pages 226-227

  Sakamoto, Kenkichi ^a   Tsutsui, Shinobu ^a   Ebata, Keisuke ^a   Kabuto, Chizuko ^a   Sakurai, Hideki ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034335694     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.226     Document Type: Article

References (27)

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2. H. Sakurai, Y. Nakadaira, M. Kira, and H. Tobita, Tetrahedron Lett., 21, 3077 (1980); H. Sakurai, Y. Nakadaira, H. Tobita, T. Ito, K. Toriumi, and H. Ito, J. Am. Chem. Soc., 104, 300 (1982); H. Sakurai, H. Tobita, Y. Nakadaira, and C. Kabuto, J. Am. Chem. Soc., 104, 4288 (1982).
3. H. Sakurai, Y. Nakadaira, M. Kira, and H. Tobita, Tetrahedron Lett., 21, 3077 (1980); H. Sakurai, Y. Nakadaira, H. Tobita, T. Ito, K. Toriumi, and H. Ito, J. Am. Chem. Soc., 104, 300 (1982); H. Sakurai, H. Tobita, Y. Nakadaira, and C. Kabuto, J. Am. Chem. Soc., 104, 4288 (1982).
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10. See: "The Chemistry of the Quinoid Compounds," ed by S. Patai, John Wiley & Sons, Bristol (1974).
11. Some silyl-substituted p-benzoquinones have been reported. See: a) H. Bock and H. Alt, Angew. Chem., Int. Ed. Engl., 6, 941 (1967).
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15. e) L. D. Foland, J. O. Karlsson, S. T. Perri, R. Schwabe, S. L. Xu, S. Patil, and H. W. Moore, J. Am. Chem. Soc., 111, 975 (1989).
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21. 0).
22. Selected structural parameters of 1 are as follows: bond lengths (Å) Sil-C2 = 1.910(2), C1-O1 = 1.225(4), C1-C2 = 1.503(4). C2-C3 = 1.354(4), C3-C1′ = 1.499(3); bond angles (deg) Sil-C2-C1 = 111.8(2), Sil-C2-C3 = 131.3(2), Si2-C3-C1′ = 112.6(2), O1-C1-C2 = 118.0(2), C1-C2-C3 = 116.9(2), C2-C1-C3′ = 123.4(2); torsion angles (deg) Sil-C2-C3-Si2 = 17.3(4), O1-C1-C2-Sil = 27.9(3), C1-C2-C3-C1′ = 20.0(3).
23. Recently, a similar highly bent p-benzoquinone derivative has been reported. See: K. Kobiro, M. Shi, and Y. Inoue, Chem. Lett., 1999, 633.
24. J. Trotter, Acta Crystallogr., 13, 86 (1960).
25. max/nm (ε) 281 (6340), 338 (6500).
26. 6 However, no such reaction was observed in the photolysis of 1.
27. K. Schaffner and M. Demouth, Photochemical Rearrangement of Conjugated Cyclic Dienes, in "Rearrangements in Ground and Excited States," ed by P. de Mayo, Academic Press, New York (1980), vol. 3.