THE STRUCTURE OF THE DIHYDRO-β-NAPHTHOIC ACIDS

May 1, 2002 - J. Am. Chem. Soc. , 1916, 38 (2), pp 400–419. DOI: 10.1021/ja02259a026. Publication Date: February 1916. ACS Legacy Archive. Cite this...
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C . G . DERICK AND OLIVER W M M .

(4) From the above facts the conclusion is drawn that the heavy high boiling fractions of petroleum contain homologs of benzene, or hydrocarbons containing the benzene nucleus. ( 5 ) The high boiling residues from the decomposition of phenyl paraffin are highly fluorescent, which supports the theory advanced in an earlier paper that the fluorescence of petroleum oils is due to the presence of complex hydrocarbons related to benzene. PITTSBURGH, PA.

[CO?TI'RIBUTION FROM

THE LABORATORY OF ORGANIC CHEbfISlXY, uNIv&RsITY OF ILLINOIS. ]

THE STRUCTURIE OF THE DIHYDRO-&RAPHTHOIC ACIDS. BY C . G. DERICX AND OLIVERK A Y Y . ~ Received December 18. 1915.

TABLEOF CONTENTS. I. Introduction. 11. The Third Isomeric Dihydro-8-naphthoic Acid. 111. Proof of the Atomic Linking Structures of the Three Dihydro-&naphthoic Acids from the Chemical Behavior of Their Respective Dibromidea. IV. Proof of the Atomic Linking Structure of the Third Dihydro-B-naphthoic Acid by Oxidation. V. A Correlation of Structure and Odor. VI. Experimental Part.

I. Introduction. Three dihydro-8-naphthoic acids which have an unsaturated linkage in the ring carrying the carboxyl group are theoretically possible, their structures being represented as follows: /CH'\CH, CaH4\ YC-CO~H

i

H (I). AI-Dihydronophthoic acid-2 .2

/CH*\CH /C-COZH I/

/cH%2H /C