Azulenes octahydro

SYNS CEDRYL FORMATE 1H-3-0-7-METHANC)-AZULEN-6-OL,OCTAHYDRO-3,6,8,8-TETRAMETHYL-, FORMATE, (3R-(3-a-3a-p,6-a-7-P,8aO-))-... 

SYNS AZULENE, l,2,3,4,5,6,7,8-OCTAHYDRO-l,4-DIMETHYL-7-(l-METHYLETHYLIDENE)-, MONOEPOXIDE 1,2,3,4,5,6,7,8-OCTAHYDRO-l,4-DIMETHYL-7-(l-METHYLETHYLIDEiNE)AZULENE-MONOEPOXIDE... 

Ethyl 6-hydroxy-l,6,7,8,9,9a-hexahydro-2H-benz[cd]azulenyl-6-acetate mixed with commercial (84.3% P2O5) polyphosphoric acid, heated 5 min. with vigorous stirring at 92-95° on a water bath, then poured immediately onto crushed ice crude l,5,6,8,9,9a-hexahydro-2H-indeno[5,4,3-cde]azulen-5-one (Y 84%) mixed with abs. ethanol, ice-cooled, stirred, treated with excess NaBH4, the ice bath removed, allowed to come to room temp., after 3 hrs. ethanol added to dissolve the precipitated intermediate cw-5-hydroxy-l,5,6,8,9,9a-hexahydro-2H-indeno-r5,4,3-cde]azulene, Darco carbon followed by ca. 0.2 M diloroplatinic acid (s. Synth. Meth. 17, 96) added, excess NaBH4 destroyed, acidified by coned. HCl, and hydrogenated at 3 atm. until Hg-uptake ceases after 4.5 hrs. cw-l,5,6,6a,-7,8,9,9a-octahydro-2H-indeno[5,4,3-cde]azulene (Y 66%). A. C. Anderson, Jr., et al., J. Org. Chem. 38, 1445 (1973) dehydration of alcohols s. a. L. A. Jones and R. Watson, Can. J. Chem. 51, 1833 (1973). 

Hydroxy-2,2,4,8-tetramethyl-octahydro-4,8-methano-azulen-l-one oxime (59) ... 

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