The Mechanism of Reduction of Conjugated Systems with Terminal

Soc. , 1939, 61 (7), pp 1854–1859. DOI: 10.1021/ja01876a064. Publication Date: July 1939. ACS Legacy Archive. Cite this:J. Am. Chem. Soc. 61, 7, 185...
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ROBERTE. LUTZAND WILLIAMG. REVELEY

1854

For characterization the aceto compound (0.15 g.) was refluxed in alcohol (10 cc.) and acetic acid (5 drops) with 2,4-dinitrophenylhydrazine (0.2 g.). The product separating in bright yellow crystals (0.24 g.) proved t o be a mixture of stereoisomers present in about equal amounts. Fractional crystallization from alcohol gave orange plates, m. p. 122-124", and yellow needles, m. p. 135-136", of the isomeric 2,4-dinitrophenylhydrazones. Anal. Calcd. for C I ~ H L ~ O ~ C,N48.98; ~: H, 4.79; N, 19.04. Found, plates: C, 48.92; H, 4.73; N, 18.89. I