J. M. Mellor et al. / Tetrahedron 56 (2000) 8019±8024
8023
crude material was puri®ed by column chromatography on
silica gel using petroleum ether±ethyl acetate (95:5) as
eluant to yield 1-nitronaphthalene (0.14 g, 81%) as a bright
yellow crystalline solid, mp 53±558C (Lit23 58±598C).
column chromatography on silica gel using petroleum
spirit±ethyl acetate (9:1) as eluant.
Column chromatography yielded 1-nitronaphthalene
(105 mg, 61%) as a yellow solid, identical to an authentic
sample.
Procedure for the reaction of naphthalene with CAN and
tetrabutyl ammonium nitrite in the presence of sulfuric
acid using methanol as solvent
Acknowledgements
To CAN (8 mmol) in methanol (20 mL) was added tetra-
butyl ammonium nitrite (1 mmol) followed by naphthalene
(1 mmol). To this was added concentrated sulfuric acid
(5 mmol) and the resulting mixture was allowed to stir at
room temperature for approximately 18 h. The reaction
mixture was washed with saturated sodium hydrogen car-
bonate solution (1£100 mL) and the products extracted into
dichloromethane (2£100 mL). The combined organic
extracts were washed with distilled water (1£100 mL),
dried over anhydrous magnesium sulfate and the solvent
evaporated. The resulting crude mixture was puri®ed by
column chromatography on silica gel using petroleum
spirit±ethyl acetate (9:1) as eluant. Column chromato-
graphy yielded the following two products.
We gratefully acknowledge ®nancial support from DERA.
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