SCIENCE. 
323 
another element than the distortion or displacement to 
which Dr. Chapman very properly refers, namely, the 
position in which the brain is held or placed. In Dr. 
Chapman’s figures, the organ rests upon the medulla, 
and upon the ventral aspects of the frontal and temporal 
lobes ; were it brought into something approximate to 
its natural position, or to the position of the human 
brain, the occipital lobes would surely project beyond 
the cerebellum to an appreciable extent. It would be 
well if the next Orang’s head should be sawn into sec- 
tions parallel with the mesial plane, and the brain figured 
in situ. 
It is gratifying to find Dr. Chapman, like Humphrey 
and Barnard, insisting that the “ scansorius ” muscle of 
Traill is really the entoglutmus. But Dr. Chapman 
does not seem to have observed the curious little muscle 
passing over the capsule of the acetabulum which Prof. 
Barnard has called “ ilio-femoralis subrectus,” and 
which, in the opossum, Coues seems to have mistaken 
for the unlucky “ scansorius.” 
A novel and significant suggestion is that, “ morpho- 
logically speaking, the laryngeal pouch of the anthro- 
poids would be homologous with and replace the two 
layers of the cervical fascia in man.” 
This otherwise very commendable paper is marred by 
some important misspellings, as of ilium which is made 
ileum twice on page 4, and by an occasional obscurity of 
style which sometimes renders the author’s meaning 
doubtful. B. G. W. 
ON THE CONSTITUTION OF THE NAPHTHA- 
LINES AND THEIR DERIVATIVES. 
(Translated from the German.) 
By M. Benjamin, Ph. B., and T. Tonnele, Ph. B.* 
Among the many aromatic hydrocarbons, naphthaline 
is one of the most interesting. The causes and laws of 
isomerism may be studied from the numerous isomeric 
compounds on one hand, while on the other, much in- 
formation is derived from the consideration that many of 
these have acquired a great importance in the technical 
arts. In consequence of this, a great number of memoirs 
exist on this subject, and they are scattered abroad 
among the numerous scientific journals. It is, therefore, 
no simple matter for one to obtain a clear survey of the 
naphthaline question. We hope that the following 
pages, comprising material originally collected for our 
own information, will be welcomed by such of our pro- 
fessional colleagues as may have occasion to study this 
subject, for we feel assured that by consulting this article 
much of their time and labor will be economized. 
CONSTITUTION OF NAPHTHALINE. 
Naphthaline was discovered in 1826, by Garden, and 
subsequently widely studied by many investigators ; yet 
its constitution remained undetermined for more than 
forty years. In the year 1866, Kekule 1 published his in- 
genious and fertile theory of the aromatic compounds, 
considering them as derivatives from a single hydrocar- 
bon, benzol. Soon after Erlenmeyer 9 so extended this 
* Note. — The following memoir, written by MM. F. Reverdin and E. 
Netting, was published in Geneva early this year. In addition to the ; 
text herewith given, the original pamphlet was supplemented with several ; 
valuable tables. These showed the derivation and behavior with reagents j 
of the various substitution products, it is with regret that we are obliged 
to omit them. The space which they would occupy, together with the 
fact that they are not of general interest, does not seem to warrant their 
insertion. The entire article is undoubtedly the best resume of the differ- 
ent theories concerning the formation of the naphthalines in existence. 
( Translators .) 
‘ Annalen der Chemie und Pharmacie, vol. CXXXVII, p. 129 (1866). 
2 Ann. Chem. Pharm., CXXXVII, 346 (1866). 
3 Ann. Chem. Pharm., CXLIX, 1 (:8 69). 
4 Ann. Chem. Pharm., CXLII, 251 (1867). Comptes Rendus, 
LXIII, 788 and 834. 
theory as to include naphthaline, which he considered as 
having been derived from two benzol rings possessing 
two carbon atoms in common. 
C C 
C C 
Graebe 3 was the first to demonstrate the correctness ot 
this theory, in the course of his remarkable researches on 
the chinones of benzol and naphthaline. Since then this 
theory has been sustained by a large number of facts, 
while no satisfactory objections have been brought for- 
ward against it. 
Other formulae have been proposed by Berthelot 4 , and 
later by Ballo 5 , and also by Wreden 6 , but none of 
these have received the approval of chemists. 
The following are the principal facts which support 
the formula given by Erlenmeyer and Graebe : 
I. The bichlornaphtochinon (Cc H 4 ) (Ci Ch O s ) yields 
on oxidation phthalic acid C 6 H 4 j c8oh ar) d a ^ so 
transformed by the action of pentachloride of phosphor- 
us into the pentachloride of naphthaline (C« H 3 Cl) (C 4 
CL) and this on oxidation produces tetrachlorphthalic 
acid Ce Cl 4 j cooh’ 
These facts prove that naphthaline is composed of 
two symmetrical rings, and that it can only have the 
formula of Erlenmeyer by the acceptance of KekuR’s 
benzol scheme. 
On the other hand, the ortho- (i, 2) position of phthalic 
acid is likewise shown which was corroborated by the 
examination of the benzol bi-derivatives (Graebe). 1 
Ladenburg 9 and Wreden 9 have objected to Graebe’s 
method of proof, on account of the derivation of tetra- 
chlorphthalic acid from phthalic being uncertain. It 
can just as well be obtained from tere or isophthalthic 
acid. This is improbable, because the tetra-chlorphthalic 
acid used, agrees in all its properties (formation of anhy- 
drides, etc.), with phthalic acid, and not with its two 
isomers.* 
II. Naphthalinetetrachloride (C 6 Hi). (C 4 H 4 Cl 4 ), 
by oxidation gives phthalic acid C« H 4 -j coyn (Laurent). 
On submitting it to dry distillation it becomes converted 
into the a and (3 dichloronaphthaline (C« H 4 ) (C 4 H» CL) 
and the latter (( 3 ) produces, on oxidation, dichlorophtalic 
acid Ce H, Cl 2 ] cooh (Atterberg). 10 
III. Monochloronaphthalinetetrachloride C„ H,, (C 4 H> 
Cl Cl) 4 may be converted into ordinary phthalic acid by 
oxidation. (P. and E. Depouilly 11 and Widman 1S .) 
Monochloronaphthaline, C 0 H, (C 4 H 3 Cl) which is the 
basis of the above compounds may be converted into 
6 Das Naphtal : n und seine Denvate. Braunschweig (1870). 
Deutsche Chem. Ges., IX, 590 (1876.) 
I 7 Ann. Chem. Pharm., CXLIX, 1 (1809.) 
8 Theorie der aromatischen Verbindungen Braunschweig. 1876, p. 36. 
9 Deutche Chem. Ges., IX. 547 (1877). 
10 Deutsche Chem. Ges. IX, 547, (1877). 
11 Soc. Chim., Paris, IV, 10, (1865). 
12 Om Naftalins Klorforeningar, Upsala, 1877, p. 16. Soc. Chim. 
Paris, XXVIII, 505, (1877). 
♦Wreden thought it might possibly have the constitution, 
ci ci 
C — C — C — COOH 
tt I II 
C — C — C — COOH 
Cl — Cl 
! that is to say, be derived from an isometric hypothetic benzol. This ii 
| however, extremely improbable. 
