Notes on scientific research. 



147 



being an unsaturated compound, would be more appropriately called laurolenic acid.) 

 Both of these still contain, linked to the tertiary carbon atom, the carbonyl of camphoric 

 acid. The other series, with a carbonyl in secondary position, includes campholytic 

 acid and isocampholytic acid (/^-campholytic acid). We now know positively l ) that 

 the bodies formerly known as lauronolic acid, isolauronolic acid, bihydrolaurolactone, 

 and isobihydrolaurolactone do not stand in a uniform relationship towards each other, 

 that is to say they are not merely differentiated by the different positions of the 

 double-bond, as was formerly assumed. They exhibit different carbon-skeletons, inasmuch 

 as camphonenic acid (VII) (iso- or /-lauronolic acid) still contains the gem. dimethyl- 

 radical of camphoric acid, whereas laurolenic acid (lauronolic acid) (XV) does not. 

 Hence, camphonenic acid is closely related to dehydrocamphoric acid (VI) on the one 

 hand and to camphonic or camphonolic acid (XIII and XI) on the other. We reproduce 

 below the atomic formulae of the principal representatives of these two series of com- 

 pounds, so far as they are at present known. 



1. Camphonene and Camphonone series. 



CH:CC0 2 H 



I 

 C(CH 3 ) 2 



I 



CH:CH 



C(CH 3 ) 2 



I 



CH 2 • CH 2 



I 



C(CH 3 ) 2 

 I 



CH 2 • C (CH S ) C0 2 H CH 2 • C (CH 3 ) • C0 2 H CH 2 • C (CH 3 ) C0 2 H 



(VI) 

 Dehydrocamphoric acid. 



(VII) 

 Camphonenic acid. 



(VIII) 

 Camphonanic acid. 



CH 2 • CHBr 



I 

 C(CH 3 ) 2 



I 

 CH 2 -C(CH 3 )C0 2 H 



(IX) 

 Bromocamphonanic acid. 



CH 2 CHNH 2 



I 

 C(CH 3 ) 2 



I 



CrVCH(OH) 

 I 

 C(CH 3 ) 2 



I 



CH 2 CH 



I 







C(CH 3 ), 



CH 2 C(CH 3 )C0 2 H CH 2 C(CH 3 )C0 2 H CH 2 C(CH 3 )-CO 



(X) 

 Aminocamphonanic acid. 



(XI) 

 Camphonolic acid. 



(XII) 

 Camphonololactone. 



CH 2 CO 



I 

 C(CH 3 ) 2 



I 

 CH 2 C(CH 3 )C0 2 H 



(XIII) 

 Camphononic acid. 



2. Laurolene and Laurolane series. 



CH 2 -CCH 3 



II 

 CCH 3 



I 

 CrVCH-CHs 



(XIV) Laurolene. 



CH 2 *C'CH3 



II 

 C-CH 3 



I 

 CH 2 C(CH 3 )C0 2 H 



(XV) Laurolenic acid. 



CH 2 CHCH 3 



I 

 CHCH 3 



I 

 CH 2 -C(CH 3 )COoH 



(XVI) Laurolanic acid. 



CH 2 C(CH 3 )(OH) 



I 

 CHCH 3 



I 

 CH 2 -C(CH 3 )C0 2 H 



(XVII) Laurololic acid. 



CH 2 C(CH 3 )— O 



I i 



CH-CH g 



CH 2 C(CH s )-CO 



(XVIII) Laurololactone. 



l ) Comp. Journ. f. prakt. Chem. II. 88 (1911), 400. 



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