1a,2,2a,6a,7,7a-Hexahydro-2,7-ethanonaphth[2,3-b]oxirene-3,6-dione
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(3b)
IR (KBr, cmÀ1): 2921, 1665, 1605, 1300, 1232, 1201, 1021; H
1
NMR (CDCl3, 300 MHz, d in ppm): 1.38 (br s, 4H), 2.61 (s, 2H),
3.01 (s, 2H), 3.17 (s, 3H), 6.60 (s, 2H); ESI-MS: 205.0786 (M + 1).
Reaction of alkenes (4a–b) with iodosyl benzene catalyzed by
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TAPFe(III)Cl in different ILs
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immobilised with 5,10,15,20-tetraarylporphyrinatoiron(III)
chloride (0.01 mmol) and the reaction mixture was stirred at
room temperature. To the reaction mixture PhIO (2 mmol)
was added in small interval of time. The completion of the
reaction was monitored by TLC, after completion, the reaction
mixture was extracted with ethyl acetate. The organic layer was
separated, dried over anhy. Na2SO4 and evaporated under
reduced pressure and purified by column chromatography to
afford the corresponding epoxides.
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2,5-Methano-1bH-indeno[1,2-b]oxirene-1b-carboxylic acid,
1a,2,5,5a,6,6a-hexahydro-6-oxo-, methyl ester (6a)
IR (KBr, cmÀ1): 2940, 1690, 1432, 1256, 1238, 1040, 850;
1H NMR (CDCl3, 300 MHz, d in ppm): 1.37 (d, J = 9.6 Hz,
1H), 1.58 (d, J = 9.6 Hz, 1H), 2.74–3.19 (m, 5H), 3.64 (s, 3H),
5.98 (d, J = 5.9 Hz, 1H), 7.27 (d, J = 5.9 Hz, 1H); ESI-MS:
221.1954 (M + 1).
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ESR analysis
The intermediates responsible for the oxidation were prepared
in an ESR sample tube by minor modification of a reported
method.42 The TAPFe(III)Cl complex (2 mM) in a [Bmim][PF6]
was placed into an ESR tube, and the solution was cooled to
À80 1C in a methanol-liquid nitrogen bath. Hydrogen peroxide
(2 equivalents) or PhIO (2 equivalents) was slowly added to the
solution. After 2 min the solution in the ESR tube was frozen to
À80 1C and was subjected to ESR measurements. An identical
reaction was performed at À80 1C in the presence of substrates
containing the electron rich and electron deficient olefins.
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Acknowledgements
The authors are thankful to University of Delhi, Department of
Science and Technology, New Delhi, for financial assistance.
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Notes and references
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c
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