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COMMUNICATIONS TO THE EDITOR
rotenone, but only on the basis of' a color test not specific for rotenone itself. Camson3has obtained a crystalline substance resenibling rotenone from a carbon tetrachloriclc solution oi the oil-free resin from the seeds. Two I;g. of ground yarn bran needs from Mexicc! were exLractctl wiih ether, the ether removed, a i d the iiisecticidally active resin (1.47;) separated froin the large atiiount of fatty oil (26.7c/c,j by partition between 90% acetic acid and petroleuiii ether. The oil-free resin in heiizene solution was iractionatetl by clironiatographic ndsorption on nlut~iina. The fraction giving a strong Goodhue' red color test deposited from benzene solution Sevcrdl crops of crystalline material giving little or no color test. The benzene was removed from the remaining solution, and the residue taken up in hot carbon tetrachloride. X heterogeneous brownish deposit formed after cotling overnight, arid was removed. On scratching the flask walls or seeding with rotenone-carbon tetrachloride solvate, a. mass of white needles was depositei, siniilx iri appearance to the rotenone solvate. Wheii warmed with alcohol, these needles were converted rapidly to thin plates like those of rotenone. 'The compound w : identified ~ as rotenone by a ni. p. of 1~64-~1&5'(cor.) both alone a i d in atlmixture with kiiwvii rotciiorie ; the formation of' a dehydro compound of t i l . 1). 222' ; optical rotation in 17, Ixiizeiie soltitiem [ u ] ? ~ D - 233'; quantitative Goodhrie and M e y r a t i d qualitative 1)urhaiii c- agreeiiieiit with the wrresponding properties ( i f authentic rotenone. Tlie isolated rotctione atiiountcd to about 0.1% (,I tlie origiiial I)eai!s. 'i'lie total niaterial giving t tie red colc~rtcst iii thic s:tniple was O.135&,cal,111atcd as rotci:orie. I t is therdore probable (list rc.itenoiic itself accounts for a substantial iwq)ortioii of the color tests reported by previous wvrkers. Some samples have beeii reported to havc a much higher content of color-producing inaterial tha:i the sample used in this work. Rotenone does iiot account fully for either the toxicity or the red color test of tlie yam bean. A riunibcr of other compounds of yet unknown constitution also have been isolated, some giving the color test, and some showiiig c1efiiiit.e toxicity to insects. Investigation of these conipounds is iiow in progress.
VOI.
ti#-,
would yield cyclohexadienes and cyc1ohex:inol. It has now been found, however, that l,&eporycyclohexane is predominantly forti!crl. I t h a also been observed that by p:using :t soliitioii of /rans-l,4-cyclohexanrdioIo i w :ic!i\,:ct.citl :111.1nii11;i a t 27,5", 7$4 of 1,d-eposycyc.lrihe~~n~ is f o i - J : i i . i i , while the cis ison:cr under similar cmilitims -,,\.e< k: only 28Yh of the epoxidc. 'The type ~i~I~:(.i1t, contact agent, and temperature used rxen influence upon the yield of the epc!xidt. 1,4-Epoxycyclohexane boils :it 120. I ;ii( I mm.), d2"4 0.9707, 1 . 4 4 i i ! .ll% ? i . i ) ; j , .1 /;(!L. Calcd. for CcHloO: C, 73.4i; H, l!j.:?O. i;ouiitl: C, 74.10; 13, 10.14. I t is soluble in tlie U S U : ~organic solvents and is partially soluble i n water, with which it forms an azeotropic niistiire boiliiiy a t 90'. It is soluble in -kO--60'z;i sulfuric acid from which it niay be reco eti 1)y tlilution 7,Yitli water. On heating with 1 bromide fmns-l,3-dibromo "
(1) V. K. Ipatieff, "Catalytic React) Temperatures," The MacMillan Cimpzi
CHPMISI R Y IJEPAKTMENT ORTII\YI..Sl E K S ~ ~ I I V P R S IY. 1
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