CLXXVI.—The isomerism of the oximes. Part II. The nitrobenzaldoximes

Oscar Lisle Brady, Frederick Percy Dunn
1913 Journal of the Chemical Society Transactions  
CIAMICIAN and Silber (Rer., 1903, 36, 4268) have investigated the action of light on the three nitrobenzantialdoximes. They found that when these substances were suspended in benzene in sealed tubes and exposed to sunlight, o-and pnitrobenza~ztialdoximes were converted into the corresponding nitrobenzsynaldoximes ; on the other hand, m-nitrobenzantialdoxime, as obtained from the aldehyde and hydroxylamine, remained unchanged. They theref ore concluded that the nitrobenzaldoximes were stable in
more » ... he syncondition, and that the m-compound, as ordinarily obtained, was in the syn-and not the anti-form as usually supposed. Goldschmidt (Ber., 1904, 37, 180) argued that m-nitrobenzantialdoxime could not have been assigned the wrong structural formula in view of other work on this compound and sought to provide some explanation of the exceptional result, without, however, repeating the work of Ciamician and Silber on the action of light. The fact that m-nitrobenzantialdoxime was found to behave differently from the 0-and p-compounds seemed so extraordinary in view of the other properties of the nitrobenzaldoximes, that the authors thought it desirable to repeat this work, more especially as, apparently, the melting points of the compounds were solely relied on for their identification. The directions of Ciamician and Silber were followed, and it was found that after ten days all three nitrobenzantialdoximes had been partly converted into t,he corresponding nitrobenzsynaldoximes. The pre-
doi:10.1039/ct9130301619 fatcat:zjdosaprgngtnjmdjicsyl2sde