Über hydrierte polycyclische Ringsysteme, III. Mitteilung: Über das Perhydro‐9.10‐benzophenanthren

Abstract

tlciiltbar durcli iiingercs Erl~ilzeii der init ;h;atriwn~celat vcrselzleii ?,Iischuiig in 1,ochendc~ii Wasser; die weiiigen 'Versuche, wclchc icii bis jcxizt auslijhrcii lionn:c, [lr,uten tlurch~veg aul' ein gunstiges Endergehnis hin. S c h l i c D l i c h e r o f f n e t , a b e r dire E n t d e c k u n g d e s L a c t o i i -: I a t ri ~i n i s i t l z e s 11 CI r 1. 1 e i n e w c i t e r e d II s s i c h t : 11. F i s c 11 e r u i i t l l ' i l o t y l 4 ) haben das nach Y o h s t und T o l l e n s bereitete M o n o l a c t o i l cl c I' a! -Z u c Ire I' s 3 I I r e niit Natriuin-anialgani reduziert zuni L a. (: t o n d e L'G 1 ii c u r o 11 s 5 LL r e , uiid sic schlieJJen daraus, daB sin der %ucker-lacfonskure da5 Carhouyl, welches von der Gluconsnure staiiiilit, die Lactonruppe erzeugtcc. Hieraus ist jetzt wcitcr zu folgern, claD incin iieu mi-'efundenes Katriumsalz Formel l haben mu13. LiiBL: sich nun tlieses, so-,-._

The Preparation, Reactions, and Properties of Triphenylenes.

“…S X X I S X S I I 2-(o-Bic~-cloliesyl)cyclohexaiione (zLX.XIII) is dehydrated in the presence of zinc chloride to the hexadecaliydrotriplieii!-leiie, which may be hydrogenated to a completely saturated octahydro derivative (182). This derivative on further treatment with bromine is converted quantitatively to 2,3,7,10tetrabromotriphenylene (XXTiII), which may be reduced to the parent compound (5).…”

“…Other studies include the molar refraction (189) 1,2,3,4,5,6,7,8,8,10 ,1 lJ2, 13,14,15,16 199 122-123 129-130 196-197 232-233 87-90 Liquid 93-94 176-177 102 .6-103.8 192-193 116.2-116.8 91-92 164-165 93-94 195.5 86.8-87.4 154-155 156.7-157.2 210-211 237-237.7 108.4-108.2 148.4-149.4 89-90 194-195 90 144 158-167 154-158 158-160 123-124 108.8-110.6 186-186.5 203.7-204.1 187-188 208-209 Other Data (141,182,193) (182) (7,8,17,81,142, 192) (17, 19, 45, 81, 164) (81) (17,100,121,142) 2.6,1~Trimethyl-1,2,3,4.5,6.7.8,9.10,1l,la- Keto-1,2,3,4,9,10,11,12- 1-1ieto-1&methyl-1,2,3,4,5,6,7,8,9,10,11,12,13,16,17,1&hexadecahyd~. . .…”

“…2-(o-Bicyclohexyl)cycIohexanone (XXXIII) is dehydrated in the presence of zinc chloride to the hexadecalrydrotriphenylene, which may be hydrogenated to a completely saturated octahydro derivative (182). Triphenylene is obtained in a variety of metalation and halogen interconversion reactions.…”

“…Schults also obtained a hydrocarbon with similar properties as a by-product in the preparation of biphenyl from bromobenzene and sodium (184). An octadecahydrotriphenylene is known (182) but not the cis-trans nature of the product. 1-Substituted derivatives are more difficult to obtain than those with 2-substituents1 presumably owing to steric hindrance effects in substitution reactions.…”

“…The stereochemistry of hydrogenated derivatives of triphenylene has apparently not been investigated. An octadecahydrotriphenylene is known (182) but not the cis-trans nature of the product. Various configurations should be capable of existence.…”