T. Tsubusaki, H. Nishino / Tetrahedron 65 (2009) 3745–3752
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1,4-dione (10). The product 10 was further purified by re-
crystallization from chloroform/hexane.
´
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4.3.1. 3-Hydroxy-1-phenylpent-2-ene-1,4-dione (10)
Colorless microcrystals (from CHCl3/hexane); mp 95–96 ꢀC; IR
(KBr)
(3H, s), 6.94 (1H, s), 7.44–8.03 (5H, m), 15.37 (1H, br); 13C NMR
(CDCl3) 25.1, 93.8, 127.8, 128.9, 133.7, 135.2, 173.6, 190.8, 197.6. FAB
n d 2.50
3400–3000 (OH), 1674, 1590 (C]O); 1H NMR (CDCl3)
d
HRMS (acetone/NBA) calcd for C11H11O3 191.0708 (Mþ1). Found
191.0749.
4.4. Silica gel-mediated decomposition reaction of 1,2-
dioxolanes 3a–h
To a solution of a 1,2-dioxolane 3 (0.1 mmol) in methanol
(10 mL) was added silica gel (Wakogel B-10, 0.5 g), and the mixture
was stirred at room temperature for 12 h. Dichloromethane (10 mL)
was added to the resulting suspension, which was filtered under
reduced pressure. The reaction flask and the silica gel were washed
well with dichloromethane/methanol (9:1 v/v), and the combined
filtrates were concentrated in vacuo. The residue was suspended
again with dichloromethane (5 mL), and filtered through a cotton
plug. The filtrate was concentrated in vacuo to give the oxirane 4.
Acknowledgements
This research was supported by Grants-in-Aid for Scientific
Research (C), No. 15550039 and No. 19550046, from the Japan So-
ciety for the Promotion of Science. We gratefully acknowledge
Professor Teruo Shinmyozu, Institute for Materials Chemistry and
Engineering, Kyushu University, Japan, for measurement of the high
resolution FAB mass spectrum.
10. (a) Nishino, H. Bull. Chem. Soc. Jpn.1986, 59,1733–1739; (b) Nishino, H.; Tategami,
S.; Yamada, T.; Korp, J. D.; Kurosawa, K. Bull. Chem. Soc. Jpn. 1991, 64, 1800–1809.
11. Snider, B. B.; Merritt, J. E.; Dombroski, M. A.; Buckman, B. O. J. Org. Chem. 1991,
56, 5544–5553.
12. Ionization potential of acetylene: 11.4 eV (calcd 11.6 eV); phenylacetylene 1a:
(calcd 9.4 eV); ethene: 10.5 eV (calcd 10.6 eV); styrene: 8.5 eV (calcd 9.2 eV);
1,1-diphenylethene: (calcd 9.1 eV). The ionization potential was referred to
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of HeI
Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Soci-
eties: Tokyo, 1981; and was also calculated by CAChe version 4.9.3.
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Soc. 1998, 19, 1080–1083; (d) Melikyan, G. G. Org. React. 1997, 49, 427–675 and
references cited therein.
14. (a) Yamada, T.; Iwahara, Y.; Nishino, H.; Kurosawa, K. J. Chem. Soc., Perkin Trans. 1
1993, 609–616; (b) Nishino, H.; Nguyen, V.-H.; Yoshinaga, S.; Kurosawa, K. J.
Org. Chem. 1996, 61, 8264–8271; (c) Nguyen, V.-H.; Nishino, H.; Kurosawa, K.
Synthesis 1997, 899–908; (d) Nguyen, V.-H.; Nishino, H.; Kurosawa, K. Hetero-
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Supplementary data
Copies of 1H NMR, 13C NMR, and IR spectra for new compounds
3a–h, 4a–h, 7h, 7i, 8i, and 10 (100 pages). Supplementary data
associated with this article can be found in the online version, at
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