ARTICLE
6 Lepley, A. R.; Thelman, J. P. Tetrahedron 1966, 22, 101–110.
Reversible Hydration–Dehydration Behavior
As described above, the hydration of 1 into 2 and the dehy-
dration of 2 to recover 1 was successfully conducted
(Scheme 4). Thus, we repeated this hydration–dehydration
7 Kawamata, A.; Kikuchi, E.; Hirama, M.; Fujise, Y.; Ito, S.
Chem Lett 1979, 859–862.
8 Schonberg, A.; Moubacher, R. J Chem Soc 1943, 71–72.
9 Bowden, K.; Rumpal, S. J Chem Res Synop 1997, 35–35.
1
cycle to evaluate its potential as a new switching system. H
NMR was conveniently used for monitoring the hydration
and dehydration reactions. The ratio between the integrated
signal intensity in the range from 5.5 to 7.0 ppm and that in
the range from 7.3 to 8.0 ppm was used as a parameter to
evaluate the conversion from 1 to 2. In Figure 9, this param-
eter was plotted against number of the hydration–dehydra-
tion cycle, which clearly demonstrated the reversible nature
of the system. Even after three cycles, deterioration of the
polymer structures was not observed by NMR and IR analy-
ses (Supporting Information Figs. S6, S7, and S8).
10 Endo, T.; Okawara, M. Bull Chem Soc Jpn 1979, 52,
2733–2734.
11 Hirama, M.; Fukazawa, Y.; Ito, S. Tetrahedron Lett 1978, 19,
1299–1302.
12 Moubasher, R.; Othman, A. M. J Am Chem Soc 1950, 72,
2667–2669.
13 Netto-Ferreira, J. C.; Silva, M. T.; Puget, F. P. J Photochem
Photobiol A 1998, 119, 165–170.
14 Silva, M. T.; Braz-Filho, R.; Netto-Ferreira, J. J Braz Chem
Soc 2000, 11, 479–485.
CONCLUSIONS
15 Mahran, M. R.; Abdou, W. M.; Sidky, M. M.; Wamhoff, H.
A novel polymer bearing acyclic vicinal tricarbonyl moieties
in the side chains 1 was developed. The tricarbonyl moiety
underwent the reversible hydration–dehydration cycle to
construct a new polymer system that exhibits reversible
changes in its properties. Applications of 1 to several revers-
ible systems such as moisture control with color indication
and control of hydrophilicity of material surface are
proceeding.
Synthesis 1987, 5, 506–508.
16 Gill, G. B.; Idris, M. H.; Kirollos, K. S. J Chem Soc Perkin
Trans 1 1992, 2355–2365.
17 Schonberg, A.; Singer, E. Chem Ber 1970, 103, 3871–3884.
18 Sharp, D. B.; Hoffman, H. A. J Am Chem Soc 1950, 72,
4311–4313.
19 Roberts, J. D.; Smith, D. R.; Lee, C. C. J Am Chem Soc 1951,
This work was supported by Grant-in-Aid for Scientific
Research (B) (21350068) from the Japan Society for the Pro-
motion of Science (JSPS), Japan and JSR Corporation.
73, 618–625.
20 For a polymer bearing cyclic tricarbonate moiety, see: Endo,
T.; Fujiwara, E.; Okawara, M. J Polym Sci Polym Chem Ed
1981, 19, 1091–1099.
21 Gonzalez-Bejar, M.; Bentama, A.; Miranda, M. A.; Stiriba, S.;
REFERENCES AND NOTES
Perez-Prieto, J. Org Lett 2007, 9, 2067–2070.
1 Rubin, M. B.; Gleiter, R. Chem Rev 2000, 100, 1121–1164.
2 Wasserman, H. H.; Parr, J. Acc Chem Res 2004, 37, 687–701.
3 Nair, V.; Deepthi, A. Tetrahedoron Lett 2006, 47, 2037–2039.
22 Li, S.; Zhu, W.; Xu, Z.; Pan, J.; Tian, H. Tetrahedron 2006,
62, 5035–5048.
23 Tatsugi, J.; Izawa, Y. J Chem Res Synop 1988, 356.
24 Rubin, M. B. Chem Rev 1975, 75, 177–202.
4 Adlington, R. M.; Baldwin, J. E.; Catterick, D.; Pritchard, G. J.
J Chem Soc Perkin Trans 1 2000, 299–302.
25 Wetz, F.; Routaboul, C.; Lavabre, D.; Garrigues, J.; Rico-
Lattes, I.; Pernet, I.; Denls, A. Photochem Photobiol 2004, 80,
316–321.
5 Goswami, S.; Maity, A. C.; Fun, H.; Chantrapromma, S. Eur J
Org Chem 2009, 1417–1426.
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