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NITRO DERIVATIVES OF NAPHTHALENE^435

did not confirm the results obtained by the above authors. Under the conditions

they described Will obtained a mixture of the 1,3,5,8- and 1,4,5,8-isomers. He
separated them by taking advantage of their different solubility in acetone. The

1,3,5,8-isomer is readily soluble even in cold acetone, while the other is insoluble

even on boiling.
Lautemann and d’Aguiar [34], by boiling 1,8-dinitronaphthalene with nitric

acid for 8 hr, obtained 1,3,6,8-tetranitronaphthalene. This result has been con-

firmed by Will.

As Patart reports, naphthalene can be nitrated to tetranitronaphthalene with

mixtures containing only a small quantity of water:

HNO 3 30-45%

H 2 SO 4 50-65%

H 2 O 5%

Starting from dinitronaphthalene more dilute nitrating mixtures may be applied :

HNO 3 10-95%

H 2 SO 4 5-80%

H 2 O 0-10%

STRUCTURE OF TETRANITRONAPHTHALENES

Will has determined the structure of the 1,3,6,8- and 1,3,5,8-isomers by direct

oxidation, or by oxidation of the products formed when reacting the isomers with

sodium alcoholate.

Oxidation of 1,3,6,8-tetranitronaphthalene:

Oxidation of 1,3,5,8-tetranitronaphthalene:

(6)

(7)