ing nicotiiie
t i ) iiornicotilie probably hy transnit~thylatioii. .Yicoiiciizu glurmz cont:~iiisprincipnlly anabasine. \\-lien grafted to *V.tnbncunz roots:' or when liyliritlizctl with the Ixtter spccies4 the leaves have 1)een rel)ortetl ti) contain predominaiitly anaba.;iiic. ICe1)etitiori oi these experiments in this !:ilxir:ttory has tliscloscd that thc supposed anaba.;iiic (IC tlic grafts a i i t l of thc hybrids is actually : t iiiisture oi ;iii:ibasine anti nornicotiiici with iisu:iliy niore ~ioriiicoti~ie than aiiabasiix, 'lhe tlificult sc.par:ition o f xiabasine from norriicotinc i r i iiiistures of the two was acconiplished by re1)vatecl fracti(ma1 crystallizativns of the picrates a i i t i of the methylated picrates after removal of iiicotine by the mcthod of Smith and '1'0 show that the iiornicotine present in the leaves t ~ these i plants actually arose in situ and at the ~.;l)enst: ~i nicotine translocated froin the roots, .\-.gla LICU scions were grafted to S.tubucunz roots. After a period of growth, a tornato scion was ::rafted to the apes of each LV,gluricu scion. Ultiinately, these three-tiered plants were examined for alkaloids. The s.glaucu scions contained one px-t of iiicotine to fifty parts of mixed anabasine ant1 iiornicotine, while the tomato scions ~ 0 1 1 taincd only nicotine. It is now clear that the replacement of the methyl group of nicotine in the plant leaf by the hydrogen :~toniof nornicotine accounts for tlie inw . u e in secondary arniiie content (previously :tt.txibutcd to anabasine4) of such graft combina1.ioiis a i i d ficnetic:ii iiybrids. It f c ) l l o ~ sthat esq)ineiit oi hybrids beI"'ctLiti(J11S' iJf t h e (le\ . ghiiica that would t i t , I1 :T. f(Zb(LCZLII2 alld iuitablr. for the ci)Iiiniercial cstr:ictitrti o f :tii:ilx-.iiie are without justificatioii. (JI \,
Schmuck, Kostrrfi a n d 1iorozilin;r. Cc~m$!. rrriil orcril
S. ( I ) o k Z ~ i d y J25, , 477
\LI.
I,l%
RESOLUTION OF 9-HYDROXYFLUORENE-LCARBOXYLIC ACID
i'. R
March, 1945
liquid 2-forrnyldecalone-l . Without distillation this was treated with isopropyl iodide and potassium carbonate in acetone according to Claisen’s method for O - a l k y l a t i ~ n . ~Almost colorless, crystalline enol ether, m. p. 67-72!’, was thus obtained in 94c0 over-all yield from decalone-l. The recrystallized 2 - isopropoxymethylenedecalone - 1 melted a t 77-78’ (cor.), and gave a slowly developing violet color with ferric chloride. A nul. Calcd. for C14H2202: C, 75.63; H, 9.98. Found: C, 75-31; H, 9.7T. Angular methylation was effected by treatment with potassium amide in ether followed by methyl iodide. The alkylated enol ether was hydrolyzed with dilute hydrochloric acid t o give 2-formyl-9-methyldecalone-1 which was separated by alkaline extraction, and cleaved to the ketone by distillation of the alkaline solution. The steam-volatile material consisted of a mixture of cis- and trans-9-methyldecalone-I obtained in about 3070 over-all yield from decalone1. Further work, as yet incomplete, indicates that this yield can be increased. The ketones were easily separated by taking advantage of the f.5) c
f
v 4uwers. Be, ,
.j0.i
N E W BOOKS
71B. 2 I ) W (1938)
differential rates of formation of the sernicarbazones.‘ Almost pure trans derivative separated rapidly, m. p. after recrystallization 218-21S.3‘ (cor.), undepressed by an authentic specimen. The cis semicarbazone, which formed slowly, melted a t 224-2255’ (cor.) after recrystallization. h mixture with authentic material’ showed no depression of the melting point. 2-Methylcyclohexanone has been converted through the sequence of reactions described above into pure 2,2-dimethylcyclohexanone,b. p. 1GG 169’; over-all yield 31%; m. p. of oxime 9393.5’ (cor.); m. p. of semicarbazone 199-201’ (cor.). Mixtures of these derivatives with samples obtained by an alternate synthesis‘ showed no depression of the m. p. The methylation step was promoted successfully with potassium t-butoxide in t-butyl alcohol.1+2 When this procedure was used in the decalone series, however, the methylation was incomplete. DEPARTMENT OF CHEMISTRY UNIVERSITY OF W I S C O Y S I ~ WILLIAMS. JOHNSON MADISON, WISCONSIN HARVEVPOSVIC RECEIVED JANUARY 22, 1945
NEW BOOKS Varnish Constituents. By H . LX’. CHATFIELD.Scieiice Publishers, Inc., 215 Fourth Avenue, New York 3, N.Y., 1941. 496 pages. 14 X 22 cm. Price, 87.00. This book contailis: a detailed description of the many diverse materials which are available for use in the manufacture of oleoresinous varnishes. There is some discussion of the methods of manufacture of some of these raw materials, especially where variations in the manufacture results in different grades or varieties which the varnish maker needs t o distinguish. The main emphasis is on the properties of the materials which influence or control their suitability for varnish making. The author evidently attempts t o give definite numerical values of measurable properties wherever feasible. A substantial fraction of the book is devoted t o t.ables in which the numerical values of Yignificant properties are systematically tabulated for easy reference arid coiriparisoti. There are such tables for L‘arnish Oils; Acids; Monoglycerides; Synthetic Resins (47 pages) ; Solvents aiid Diluents (22 pages) ; Plasticizers f l t i pages); Driers, Salts and Soaps; Asphaltums and Pitches, U’axes: besides uumerous small tables of varied yorts. Sumerous referenrcs to the technical and patent literature are given. The test contains much descriptive iiiatter and comments on perfurniance and usefuliiess of the materials with a discussioii of the possihility of suhstitutiori of OM material tJY another and the influence of such replacements on the properties of the finished varnish. Since these comments are written by a n experienced English expert they should be of value to American formulators in these days when shortages of materials and priorities may make substitutions necessary. Statistical data as t o production and international commerce in these materials are omitted and what little comment there are on such questions is a p t t o he weak. Thus iiiirlc.r t h e heading Soya Hean Oil he says, “The oil is o t b t a i v w l froin t h r I i w i i < o f (:lv
