146 



Report of Schimmel s$ Co. April 1913. 



camphoric acid, when boiled with soda-liquor, gives rise to hydroxy-3-camphoric acid 

 lactone. The bromo-3-camphoric acid with high m. p. was decomposed by prolonged 

 heating of its neutral soda- salt in aqueous solution, giving rise to hydroxy-3-iso- 

 camphoric acid and camphonenic acid. When dehydrocamphoric acid chloride is 

 heated with bromine in a sealed tube there ensued a reddish-coloured syrupy mass, 

 which was converted by decomposition with sodium carbonate into an acid containing 

 two hydrogen atoms fewer than laurolenic acid 1 ) and which for this reason was called 

 dehydrolaurolenic acid. 



For the nomenclature of substituted camphoric acids, Bredt has adopted the notation 

 of the cyclic carbon atoms, as previously drawn up by von Baeyer and more recently 

 by Grignard' 2 ). In common with camphor, camphoric acid contains the camphoceane- 

 (trimethyl pentamethylene-)ring (\) s ). The camphoric acid derivatives substituted for 

 the two gem. methylenes Kipping denotes with the letter it. For the designation of those 

 derivatives of camphoric acid in which the substitution occurs in the third methyl in 

 end-position, Bredt proposes the letter Q. As an example of this notation he cites 

 the four monobromocamphoric acids which are known up to the present. These are 

 bromo-3-camphoric acid (II) to which reference has been made above, bromo-4-camphoric 

 anhydride (III), ^-bromocamphoric acid (IV) 4 ) and the acid which has been obtained by 

 Armstrong and Lowry 5 ) from the oxidation of /?-bromocamphor, which possibly may 

 represent the ^-bromocamphoric acid (V). 



CH 2 *CH 2 



I 

 C(CHs), 



I 

 OrVCH-CH 8 



(I) Camphoceane ring. 



[4] 



^CHBrCHC0 2 H 



™ C(CH 3 ) 2 (^) 



i2i CH2 _m<:_co 2 H 



CH 3 (£) 



(II) Bromo-3-camphoric acid. 



CH 2 • CBr-CO 



C(CH 3 ) 2 >0 



CH 2 -C — CO 

 CH 3 



(III) Bromo-4-camphoric anhydride. 



CH 2 • CHC0 2 H 



I 

 H 3 CCCH 2 Br 



I 

 CH 2 • CC0 2 H 



CH 3 



(IV) Tt-Bromocamphoric acid. 



CH 2 CHC0 2 H 



I 

 C(CH 3 ) 2 



CH 2 CC0 2 H 

 CH 2 Br 



(V) i2-Bromocamphoric acid. 



In an article on new methods of preparing camphonenic acid (/-lauronolic acid) 

 and its relations to laurolenic acid (lauronolic acid), which has been published almost 

 simultaneously with the above, Bredt 6 ), while as far as possible adhering to existing 

 conditions, has removed a maze of designations which has already given rise to 

 continual confusions and errors, and would have continued to do so. This applies 

 principally to the designations lauronolic acid and campholactone, which are hence- 

 forth abolished. Bredt starts from the following points of view: — At the present time 

 we have knowledge of two series of unibasic unsaturated acids derived from camphoric 

 acid. To the one series belong camphonenic acid and lauronolic acid. (The latter, 



x ) For the nomenclature see below. — 2 ) Comp. Report October 1912, 143. — 3 ) IAebigs Annalen 299 

 (1897), 162. — 4 ) Kipping, Journ. chem. Soc. 69 (1896), 918. — 5 ) Ibidem 81 (1902), 1467. — •) Journ. f. 

 prakt. Chem. II. 87 (1913), 1. 



