~ 
“Note: s ON SCIENTIFIC RESEARCH. Lee wn Sie ATES 
: "Chemical Notes. o ee 
Se For he peneemcats occurring in pentaceanic cyclic Systems by splitting off 
ater or hydrogen chloride, FE Ruzicka *) suggests the term of Wagner’s rearrangement?), 
‘Si ice Wagner -was the first to. give a correct interpretation of the well-known trans- 
position. of this class, 2. e. the transition of borneol to -camphene.. This camphene 
Sala would then be a special case of Wagner’s rearrangement. ; 
This transposition allows to pass from the ‘ ‘camphor type” to the “fenchone EIREs 
. bd vice versa, as is illustrated by the following formula: mast 
ey eae eee ee as GH 
HAC = ~~ CHOH ERC a Lon eeu COO e er SCO 
q Me 2 C(CH,)2- a bho | ee oxid. > CH | ‘ 
eee cs Hc! SOICICHs = FCs es NCrCH 
ee 
3 25 CH LE pie Ne ar CH eeeeagt CH a ee } 
i - Borneol  _ = ey - Camphene 5 . Camphenilone | 
oe € (Camphor type). obs ee ce -Fenchone type. . 
Bence | chon? Hc, oe : be cH | Hee go bOn 
a | CH, | 2 H,0>- | saa -oxid. > C(CHs)2 
Betc |: -C(CH): Hac CH HCE) ery 
Bie ee a cane ee ee ; 
= : -Fenchylalcohol a-Fenchene PRET it Re uee EE hee adnate ey 
as _(Fenchone type). nS, shi at = : oo type. | 
3 In order to explain the Wagner rearrangement, two assumptions have beak trade. 
Ecos to the first, there is primarily formed on abstracting water from borneol | 
an unstable body, i. e.. tricyclene®); according to the other, a body | with a. bivalent 
carbon atom*). By splitting one of the linkings in the tricyclic ring, the tricyclene 
should pass over directly into camphene, whereas the body with the bivalent carbon : 
tom would first have to undergo a Realy aneetiont of the carbon bonds. ea ere 
_ The question which ofthetwo ~ ; i pela ; . 
 Lanvations is correct, might, in C: CH; : i Php C-CH, . 
k Be shin pe casty solved HC SSG LS cel HL C Cor oe Lax 
in favour of the formation of tri- | | | ie < AS 
cyclene in case it would be pos- Clery ee CCCs 
© sible to prove that Wagner’s re- Bene hl vee CH, c 9 ae ee CH: 
arrangement occurs also with a a CH j ya ; CH 
rtiary alcohol, since with such : Tapyelece: 
Z a body no bivalent carbon atom 
a appear. Ruzicka actually CONG Toe in proving that with fe aiden ol Sad methyl- 
fenchyl alcohol, obtained from camphor or fenchone according to Zelinski®) by treat- 
ment with methyl magnesium iodide, the splitting- -off of water is connected with Wagner’ Ss 
earrangement, : so that Hieyelone must be een as intermediate product. 
3 
p>: 2) Havctict chimica acta 1 1918), 10." ZY, nes Russ. phys.-chem. Soc. 81 (1899), 680. — %) Comp. 
Sen emmler, Die titherischen Ole, Leipzig 1906, vol. Ill. p. 111. — 4) Meerwein, Liebig’s Annalen 405 (1914), 133. - 
- “ay Berl. Berichte 34 00) 2877, 2883. ; ' : 
Q* 
