1 -Hydroxy-1,2-dihydro-naphthalene

Cyclohexadienol was prepared by Rickborn in 1970 from reaction of the epoxide of 1,4-cyclohexadiene with methyl lithium.100 A hydrate of naphthalene, 1-hydroxy-1,2-dihydro-naphthalene was prepared by Bamberger in 1895 by allylic bromination of O-acylated tetralol (1-hydroxy-l,2,3,4-tetrahydronaphthalene) followed by reaction with base.101 Hydrates of naphthalene and other polycylic aromatics are also available from oxidative fermentation of dihydroaromatic molecules, which occurs particularly efficiently with a mutant strain (UV4) of Pseudomonas putida.102,103 The hydrates are alcohols and they undergo acid-catalyzed dehydration to form the aromatic molecule by the same mechanism as other alcohols, except that the thermodynamic driving force provided by the aromatic product makes deprotonation of the carbocation (arenonium ion) a fast reaction, so that in contrast to simple alcohols, formation of the carbocation is rate-determining (Scheme 6).104,105... 

Dimethyleneperoxidecarbamide. See Vol 5, D1337-R 7-Hydroxy-1, 2-Dioxo-l, 2-Dihydro-Naphthalene. See this Vol, N20-R... 

Cyano-1-hydroxy-6-me thoxy-tetralin, 52, 96 Cyanomesitylene, 50, 54 1-CYANO-6-METHOXY-3,4-DIHYDRO-NAPHTHALENE, 52, 96... 

Reaction of dimethyloxosulfonio- and triphenylphosphonio-substituted (3-oxocyclohex-l-enyl)methanides with 2,3-diphenylcyclopropenone gave 8-hydroxy-6,7-diphenyl-3,4-dihydro-naphthalen-l(2//)-ones 6. ... 

The Pechmann reaction of 1,6-dihydroxynaphthalene (459) with 3,5-diethoxycarbonyl-l,2-cyclopentanedione led to compound (460), which, on decarboxylation, formed a derivative of 11-oxaequilenin (461). By this method 1,7- and 1,5-dihydro naphthalenes were converted into the 2-hydroxy- and 4-hydroxy analogs of compound (461), respectively [558]. 

The 1,2-shift in the dehydration of rranj-l-hydroxy-2-ethylthio-l,2-dihydro-naphthalene, a simple model for the glutathione-naphthalene 1,2-oxide adduct (the so-called premercapturic acid which is receiving considerable attention because of the importance of arene oxides in metabolism), leads to ethyl 1-naphthyl sulphide via a cyclic sulphonium ion, ... 

CiftHijNOjS 42399-49-5) see Diltiazem (4S)-3,4-dihydro-4-hydroxy-2-(3-methoxypropyl)-2H-thieno[3,2- ] 1 2-thiazme-6-sulfonainide 1,1-dioxide ( 10 16 2 65 154127-42-1) see Brinzolamide ( )-3 ,4"-dihydro-r-hydroxy-7 -methoxyspiro[cyclOpen-tane-l,2 (l -naphthalene]-r-acetonitrile (CirHjiNO 57 797-09-9) see Butorphanol 23-dihydro-3 hydroxy-l methyl-l indole-5,6-dione (C9H9NO3 54-06-8) see Caibazochrome... 

Condensation of 7-methoxy-3,4-dihydro-1(2H)-naphthal-enone with tetramethylene dibromide by means of NaH in benzene or tert amyl alcohol gives 3,4-dihydro-7-methoxy-2,2-tetramethylene-1(2H)-naphthalene (bp (0,05 mbar) 120-123 °C), which is treated with acetonitrile and butyllithium in THF yielding 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-2,2-tetramethylene-1-naphthalene-acetonitrile (mp 140-142 °C). This compound is reduced with LiAIH4 in THF to afford hydro-2,2-tetramethylene-1-naphthol (mp 178-180 °C), and isomerized to 4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxy-phenantrene i (mp 187 °C). 

A method frequently used to determine aromatic amines in water-soluble dyes involves their extraction with chloroform, followed by diazotization of amines and coupling of diazonium salts with a reagent R-salt (disodium-3-hydroxy-naphthalene-2,7-disulfonate) or pyrazolone T (4,5-dihydro-5-oxo-l-(4-sulfophenyl-)l/7-pyrazole-3-carboxylic acid). The separated products are detected by UV-VIS spectrophotometry or fluorescence (210-212). 

Staggered configurations have also been observed for the tricarbonyl chromium complexes of phenanthrene 294, 295), 9,10-dihydro-phenanthrene 293, 295), anthracene 202), naphthalene 262), and 1-aminonaphthalene 58). The eclipsed configuration has been observed for the tricarbonyl complexes of anisole (57, 229), toluidine 60, 61), methylbenzoate (59), o-methoxyacetylbenzene, o-hydroxyacetylbenzene 101), 2-methoxy-[l-hydroxy-ethyl]benzene (99), and 2-methyl-[l-hydroxy-l-phenylpropyl]benzene (97). It is apparent that the orientation of the chromium tricarbonyl moiety is in many cases controlled by the substituents on the ring to which it is coordinated, and this has been attributed to mesomeric electron repulsion or withdrawal by the substituents 374). 

Aromatization of preMAP Metabolites. Another spontaneous aromatization process has been observed for preMAP metabolites. PreMAP metabolites of naphthalene (77) and phenanthrene (78) have been shown to spontaneously aromatize to the parent hydrocarbon. The decomposition of 9,10-dihydro-9-hydroxy-10-( cysteinyl)phenanthrene has been proposed to occur through a thiiranium ion as shown in Equation 14. The isolation of the 9,10-dihydrodiol, and a phenol... 

Figure 1. Catabolic pathways for degradation of naphthalene by bacteria. I, naphthalene II, cis-l,2-dihydro-l,2-dihydroxynaphthalene (naphthalene dihydrodiol) III, l,2-dihydrox3maphthalene IV, 2-hydroxy-chromene-2-carboxylate V, mns-o-hydroxybenzyIidene pyruvate VI, salicylaldehyde Vn, salicylate VIII catechol IX, c 5,ci8-muconate semialdehyde X, cis,ci8-muconate XI, gentisate XII, maleylpyruvate.

Dimethylaminopyridine 4,6-Dinitro-o-cresol Diphenylamine Disodium octaborate tetrahydrate Endosulfan Ethiofencarb 6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline 2-Ethylhexanal Ethyl hexanediol 2-Ethylhexenal 2-Ethyl-2-hexenal Ethyl-p-nitrobenzoate Etrimfos Fenamiphos Fenpropathrin Fenthion Fluometuron Furfural Glyoxalic, acid Hexachloro-1,3-butadiene Hexachloroethane Hydramethyinon 2-Hydroxy-2-methylpropanenitrile 2-Imidazolidinone lodofenphos Isofenphos Isooctyl thioglycolate Isopropanolamine Kojic acid Laurie acid Lead acetate Lead acetate trihydrate Lead naphthenate 2,6-Lutidine Mecarbam Mercury chloride (ic) Metam-sodium P-Methylnaphthalene Naphthalene Nicotine Oxamyl Parathion-methyl Pentaerythritol Perchloropentacyclodecane Permethrin Phenothiazine Phenylmercuric acetate Phorate Phosalone Phoxim Phthalic anhydride a-Pinene Pine (Pinus palustris) tar oil Piperazine Piperazine dihydrochloride... 

Tetrahydrofuran ring. An aq. soln. of l,2-dihydro-2-hydroxy-7-methoxy-czs-l,2-dimethyl-l-(2-dimethylaminoethyl)naphthalene methiodide digested 20 min. with thallous hydroxide on a steam bath -> l,2,3a,9b-tetrahydro-8-methoxy-czs-3a,9b-dimethylnaphtho[24-b]furan. Y 78%.—Thallous hydroxide proved to be superior to silver hydroxide. F. e. s. E. L. May and H. Kugita, J. Org. Ghem. 26,188 (1961). 

---