x OTEh
September 1969 room temperatiire, the liqiiid moiiomer deposited a solid, which was collected by filtration and dried (P20:) in vacuo. Since the C1 coiiteiit of the solid (found, 24.1) was the same as t h a t of the liquid (foulid, 24.0: theory, 24.2), the solid is presumably a rlimrr 01' higher intermolecular coordination polymer of If. 2-Diethylamino-1,3,2-diheteroboracycloalkanes(IIIa-f).The appropriate 2-chloro dei,ivative (Ia-f) was cooled to -70" aiid treated drupwise with excess EtJYH. The mixture was nllowed to warm to room temperature, stirred cautiously until the exothermic reactioii siibsided and, then, vigorously for 1 hr, aiid filtered to remove a precipitate. Distillation of the appropi,iate filtrate gave the prodiictr IIIa-f (Table 111).
Acknowledgment.-The authors express their appreciation to Drs. JV. ,J. Barrett, W. C. Coburn, Jr., 1'. D. Sternglanz, and associat'es for microanalytical and spectral determinations and to N r s . Martha Thorpe for nmr data. Some of the analyses were performed ky. Galbraith I,aboratories, Knoxville, Tenn.
Compounds Related to Insect Juvenile Hormone. IV N. \V.II~.IB.~Y.ISHI,P. E. SONSET,A N D 11.W.L.\w - I yricultural liesearch Service, C . S . Department o j dgriculture, Entomology Research Division, Beltsville, Jlaryland 30705
Received February 28, 196b
The juvenile aiid most compounds that have JH activity by the bioassay with Tenebiio molifor L. are acyclic sesquiterpenes or modified sesquiterpe1ies3-~with an array of trisubstituted double bonds every fourth carbon. The purpose of the present work was t o assess the JH activity of compounds in which some or all of t'he double bonds and/or alkyl side chains were eliminated to discover easily preparable JH mimics. Table I lists the compounds and the minimum n-eight (rig) that caused detectable retention of juvenile characteristics. The cecropia JH and methyl farnesate 10,ll-epoxide are included as references. The removal of either unsaturatiori caused a drastic reduction of activity.g The conversion of squalene ria its epoxide to cholesterol and the facile transformations of model acyclic terpenoids to cyclic, bicyclic, and polycyclic materials have been well documented. These results prompted us to heat our mixture of the synthetic JH isomer and the closely related met'hyl farnesate l0,ll-epoxide with acid while conditioris were controlled so as to produce mixtures rich in either mono- or bicyclic compounds. These materials were quite inactive. lo Therefore, ( 1 ) IT. ltiiller. I. A. Champhell, C. S. Fraiikliii, 1.2. S . l l o i y y i i , :tiid I ) . *J. Tivey, ,J. ( ' / i f /H. Soc., 114.5 (l9.5X). 0 . Tsiige, 11. Sishinohara, and 11. Tashiro, Hi!//. Chrni. Soc. Japan, 36, 1477 11963); Chewz. .lbslr., 60, 5455 (1864). T. 1). Perriiie aiid L. J. Hargeiit, -1. Org. Chrm., 14, .5X3 (1949).
scheme employed begins with 9-chloroacridines and is essrntidlv as reported by Bergmann, et a1.* The det,ails
dried (30 g crude), and recrystallized from JIeCN: yield L"2 g (30'%).
(1) We gratefully acknowledge t h e support of this investigation by t h e
(3) T. S. Osdene, P. 13. R U H ~ Ianil , I.. Itnnr. ./. .We(/, C ' h r m , , 10, 131 I!Mi), (4) E. .I. Gerberu. 1,. T. I
