F--induced decomposition of 3-[(tert-Butyldimethylsiloxy)phenoxy]-3-phenyl-1,2- dioxetanes without C-C bond cleavage of the dioxetane ring

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8947-8950

  Matsumoto, Masakatsu ^a   Azami, Mitsunori ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE;

ARTICLE; BIOLUMINESCENCE; CHEMOLUMINESCENCE; CONTROLLED STUDY; DECOMPOSITION; DRUG SYNTHESIS; ELECTRON; LIGHT; OXIDATION REDUCTION STATE;

EID: 0030735716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10359-8     Document Type: Article

References (26)

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15. A pivaloyl analogue of 3 has very recently been synthesized; Akhavan-Tafti, H.; Eickholt, R. A.; Arghavani. Z.; Schaap, A. P. J. Amer. Chem. Soc. 1997, 119, 245-246.
16. The singlet oxygenation of 4a proceeded sluggishly at -78°C.
17. 1HNMR analysis of a mixture after treatment of 5a with TBAF in DMSO-d6.
18. To isolate a fragment (quinone) derived from a phenoxide part of 5, we attempted to synthesize an analogue bearing a t-butyl-substituted phenoxide in place of an unsubstituted phenoxide in 5a. However, the singlet oxygenation of the corresponding ethylene gave a complex mixture including little of the desired dioxetane.
19. +, 0.7), 214 (100), 150 (23), 105 (47).
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24. 13
25. Adam, W.; Heil, M. Chem. Ber. 1992, 125, 235-241.
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