ae ‘paper by. A. Michael); force, The Relations between the chemical Structure 
bok. Carbonyl Derivatives and their Reactivities towards Salts of Semicarbazide”. In 
tl is paper, which is unsuitable for short abstracting, a theory for these interactions 
‘is put forward. The ketones investigated and ranging within our scope of interest 
x were: — methyl amyl ketone, methyl hexyl, -octyl, --nonyl ketones, ethyl amyl ketone, 
4 cyclohexanone, ‘and ap phate LA pal the following aldehydes were in- 
vestigated: cen bey acide, anisic, and 
cinnamic aldehydes, 
SMe adathor. — The parent OS ee nupleclvade all derivatives of the camphor 
series, 1. €. ; mor-camphor ay). = bicyclo(1. 22 heptanone-2, from which camphor, fenchone, 
3 -camphenilone, and fenchocamphorone are derived, was hitherto unknown. A synthesis of 
this interesting body has now been published by S. V. Hintikka and G. Komppa’*). After 
_ several unsuccessful attempts they resorted to Reformatzky’s reaction and condensed 
" 
ere) yo ee CH. COLCoHs eae | 
ae CHa} agai: ch, 2 + Zn-+ BrCH.CO.CH ae a 
H.C ee) Poe He ? aM 
oes ‘ Pee ei Ole ara Pecan Maines, 
: es. (I) Norcamphor. teal ae (Il) Ethyl eyclopentanone carboxylate. | ie 
fo 6, EE CO.CHs cee aga ah, CO,GHs214) 
Si ; aE 1.0 ge nc alan \ 
| C(OH)-CHy:COsCH,  \ Oe CH. CO. CH Ye 
me ay Methy! ethyl hydroxy-homo- (IV) “Methyl ethyl dehydrohomo- 
is norcamphorate. eee: norcamphorate. 
. | CH-CO2C3H; ¥) i I CH-CO.H 
a ; CH, : abies ah cK ie iCH: Cass 
zy Pes eid, “HC ee ; 
CCH. CO,CHs ay de CH CHec COSE 
: (Vv) Methyl. ethyl homo-norcamphorate. pe CD) Homo-norcamphoric acid. 
ethyl cyclopentanone carboxylate (II) with methyl bromoacetate, when atau ethy!] 
_hydroxyhomonorcamphorate (III) resulted. By abstracting water this ester yielded. methyl | 
ethyl dehydrohomonorcamphorate (IV) which on addition of hydrogen passed over 
readily into methyl ethyl homonorcamphorate (V). From this ester, there resulted, on 
Saponification, homonorcamphoric acid (VI), the lead salt of which yielded, by dry 
' distillation, the nor-camphor looked for. 
_ For the preparation of ethyl hydroxy Ai ei a ethyl 1:3- -cyclopentanone 
carboxylate and methyl bromo acetate were heated, in benzene solution, with zinc shavings. 
' The ester (III) was a colourless oil which on heating with sodium hydrogen sulphate 
lost water with formation of methyl ethyl dehydrohomonorcamphorate (IV); b.p. 143 
to 145° (13mm.). This ester, on reduction with colloidal platinum or palladium, gave 
m <a: ethyl homonoreamphorate ); b. p. 135 ‘to 141° 3 ye By saponification, 
_*) Journ. Americ. chem. Soc. 41 (1919), 393, _ 2) ‘Conceching the nomenclature of the camphor derivatives, 
see G. Komppa, Berl. Berichte 42 (1909), 898. — %) Annal. Acad. Scient Fenn., Series A. 10 (1919), No. 22. 
