Synthesis and chemiluminescence of 3,3-diisopropyl-4-methoxy-4-(2-naphthyl)-1,2-dioxetanes

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 411-414

  Matsumoto, Masakatsu ^a   Watanabe, Nobuko ^a   Kobayashi, Hisako ^b   Azami, Mitsunori ^a   Ikawa, Hiroshi ^b  

^a KANAGAWA UNIVERSITY   (Japan)

^b Central Research Laboratories   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIOXETANE DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMOLUMINESCENCE; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0031030444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02312-X     Document Type: Article

References (19)

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3. Beck, S.; Köster, H. Anal Chem. 1990, 62, 2258 -2270.
4. Adam, W.; Fell, R.; Schulz, M. H. Tetrahedron 1993, 49, 2227-2238.
5. Matsumoto, M.; Suganuma, H.; Katao, Y.; Mutoh, H. J. Chem. Soc. Chem. Commun. 1995, 431-432.
6. Schuster, G. B. Acc. Chem. Res. 1979, 12, 366 - 373. See also Catalani, L. H.; Wilson, T. J. Amer. Chem. Soc. 1989, 111, 2633 - 2639.
7. Schuster, G. B. Acc. Chem. Res. 1979, 12, 366 - 373. See also Catalani, L. H.; Wilson, T. J. Amer. Chem. Soc. 1989, 111, 2633 - 2639.
8. 8 have called the substitution pattern of a naphthyl of 2a 'odd' ; an 'odd' pattern is one in which the donor's(O-) point of attachment to the acceptor (dioxetane ring or C=O of emitter formed by the decomposition of a naphthyldioxetane) is such that the total number of ring carbon atoms separating these points, including the atoms at the point of attachment, is an odd whole number. According to the above definition, m-phenoxide-substituted dioxetane (1a) is 'odd' patterned.
9. Edwards, B.; Sparks, A.; Voyta, J. C; Bronstein, I. J. Biolumin. and Chemilumin. 1990, 5, 1 - 4.
10. Matsumoto, M.; Suganuma, H.; Azami, M; Aoshima, N.; Mutoh, H. Heterocycles 1995, 41, 2419-2422.
11. McCapra, F. Tetrahedron Lett. 1993, 34, 6941 -6944. See also ref. therein.
12. Edwards, B.; Sparks, A.; Voyta, J. C.; Strong, R.; Murphy, O.; Bronstein, I. J. Org. Chem. 1990, 55, 6225 - 6229.
13. It has very recently been found that, for thermally stable dioxetanes bearing a phenolic substituent, introduction of an alkoxymethyl at the vicinal position causes emission of flash-like intense light; Matsumoto, M.; Watanabe, N.; Kobayashi, H.; Suganuma, H.; Matsubara, J.; Kitano, Y.; Ikawa; H.Tetrahedron Lett. 1996, 37, 5939 - 5942.
14. All the dioxetanes synthesized here gave satisfactory spectral data and were stable enough to permit handling at room temperature and could be stored in a refrigerator without decomposition for > 1 y.
15. Matsumoto, M.; Watanabe, N.; Arai, N. Tetrahedron Lett. 1996, in press. See also ref. 3.
16. Synthesis of a (l-siloxy-2-naphthyl)-substituted dioxetane could not be attained, unfortunately, because the McMurry coupling of methyl naphthalene-2-carboxylate bearing a 1 -oxy-functionality such as methoxyl with diisopropyl ketone afforded an ethylene bearing an unsubstituted 2-naphthyl and only a trace amount of the corresponding ethylene.
17. McCapra has described briefly on explanation for the difference in half-life of emission between dioxetanes such as 1a and 1b in ref. 10.
18. The parameters cited in the following report were used; Klemm, L. H.; Shamtai, J.; Taylor, D. R. J. Org. Chem. 1968, 33, 1480 - 1488.
19. The HOMO electron density at the adjacent carbons of Cα may also participate for the charge transfer.