— 124 — 



Formula I could then immediately be converted, by disruption of 

 the tri-ring, into a ketoalcohol, and the latter, by loss of water, yield 

 an unsaturated ketone : 



NEL 



CH, 



CO 



-CH 3 ► > C - C C >~ CH 3 



CH 3 / X / 



If pulegone hydroxylamine is dissolved in concentrated acids and 

 heated to 50 to ioo°, a mixture of bases is obtained, from which 

 after purification a crystallising picrate can be obtained, which on 

 decomposition yields the base C 10 H 17 NO, boiling point 9i°(8mm. 

 pressure); d 20 o 0,9731; « D -f- 37 10 '; n D 1,4757. This body is a 

 weak base, which gives nearly all alkaloid reactions. Its ketone 

 character could be proved by formation of an oxime (melting point 1 8o°) 

 and a semicarbazone (melting point 153 to 154 ). As its benzene 

 sulpho-compound (melting point 120 ) does not dissolve in alkalis, 

 it is here a question of a secondary base. The hydrochloride could 

 not be produced in the pure state, and for this reason no nitroso 

 compound could be obtained. On reduction with sodium and alcohol, 

 the base absorbs 4 atoms hydrogen and is converted into the tetra- 

 hydro base C 10 H 21 NO, boiling point i34°to I35°(i8mm.); d 0,9646; 

 no 1,4815. The latter does not yield a readily soluble picrate, but 

 on the other hand, yields a carbamate. If the base C 10 H 17 NO is 

 reduced with zinc dust and hydriodic acid, only two atoms hydrogen 

 are added, with formation of the base C 10 H 19 NO (boiling point 106 , 

 1 1 mm. pressure); d 20 o 0,952; « D — 5 ; n D 1,4727. 



With regard to this work C. Harries and L. Roy 1 ) state that 

 they have also obtained from pulegone hydroxylamine, by heating 

 with 20 per cent, hydrochloric acid, the base C 10 H 17 NO. 



For the further elucidation of the constitution of this body, 

 Semmler 2 ) endeavoured to determine whether it is here a question 

 of a dicyclic system, or whether after primary formation of the same, 

 ring-disruption with formation of a double-linking has again taken 

 place. Chiefly on account of the experimentally confirmed fact that 

 the same above-mentioned tetrahydro base C 10 H 21 NO is also obtained 

 by reduction of two bodies whose constitution is established, viz. 

 pulegone hydroxylamine and pulegone amine, he arrives at the con- 

 clusion that the above-named formula I belongs to the base C 10 H 17 N O. 

 The following graphic formulae illustrate what has been said: 



x ) Berl. Berichte 37 (1904), 1341. 

 2 ) Berl. Berichte 37 (1904), 2282. 



