— 148 — 



alcohols, fenchone, fenchene polymerides) it could not be converted 

 into the solid inactive chloride boiling at 76 to 7 8° 12 (mm. pressure) 

 which is stable towards silver nitrate. 



The experiments made by the authors showed that hydrochloric 

 acid has practically the same action on both acetates. The slight 

 deviations observed in fenchyl acetate are explained by the assumption 

 of a greater tendency to isomerisation. 



Kondakow 1 ) has also examined some derivatives of isofenchyl 

 alcohol. This alcohol, the member of the fenchane series which has 

 hitherto been examined least of all, is, according to some investigators, 

 a mixture of chemically identical, but optically differing, alcohols; according 

 to others, it is a mixture of tertiary, or of tertiary and secondary alcohols; 

 or a stereomeric fenchyl alcohol; or finally a mixture of a liquid fenchyl- 

 alcohol and a solid stereomeric isofenchyl alcohol. The reactions 

 known up to the present do not admit of a decision either one way 

 or the other. 



Kondakow produced from several fenchenes of different rotatory 

 power, according to his zinc chloride method, the acetic ester of iso- 

 fenchyl alcohol. The resulting alcohol was a mixture of a solid body 

 (m. p. 61,5 to 62°, Md — 25,73°) and a liquid isomeride (di 5 o 0,963; 

 n D 1,48008; «d — 13° 44'; b. p. 88 to 88,5 [10 mm. pressure] and 

 97 to 98° [13 mm. pressure] respectively). The acetates were partly 

 dextrorotatory (M D -j- 5 33'), partly laevorotatory (Md up to — 9 35 ), 

 and partly inactive, and had approximately the same constants : 

 d^ 0,9752 to 0,9784; n D 1,46168 to 1,46257; molecular refraction 

 48,34 (inactive acetate) to 55,07 (d-acetate); b. p. 95 to 97° (i-acetate); 

 90 to ioo° and 100 to 105° (1- and d-acetates respectively; 15 mm. 

 pressure). From the 1- and the i-acetates, laevorotatory alcohols were 

 obtained which contained in their first fractions inactive portions 

 remaining liquid; the subsequent portions were solid (m. p. 48 to 53°, 

 54 to 55°), and laevorotatory. In the various hydrations there always 

 remained behind a portion of the fenchene amounting to about 10% 

 of the quantity worked up, whose rotation, boiling point, and specific 

 gravity were lower than those of the original material. The experi- 

 ments showed that there exist on the whole no definite relations 

 between the acetates and the corresponding alcohols, except that the 

 acetates had approximately the same, and the isofenchyl alcohols 

 different rotations. Optically inactive isofenchyl alcohol of the b. p. 

 80 to 8i° (pressure not mentioned) yielded, on treatment with phos- 

 phorus pentachloride, a chloride of the b. p. (of the bulk) 73 to 74° 

 (9 mm. pressure) ; d 2 o° 0,996 ; n D 1 ,48 1 2 ; M D — 3 53'; molecular refraction 



*) Journ. f. prakt. Chem. II. 75 (1907), 539. 



