Tetralin 1,2-epoxide

Naphthalene 1,2-oxide (45) has been obtained by bromination (NBS)-dehydrobromination (DBN) of tetralin 1,2-epoxide (115).57 Sodium in liquid ammonia gives diepoxide 116 from 117.58 Also, the saturated compound 118 with potassium f-butoxide in THF yields the oxaazabis-6-homobenzene system (119, 80%).29... 

Naphthalene 1,2-oxide. Yagi and Jerina3 have reported a new method for synthesis of arene oxides. The starting material for the preparation of naphthalene 1,2-oxide (5) is l-hydroxy-2-bromotetralin, (1), which is acetylated with trifluoroacetic anhydride in chloroform to give (2) in 84 %yield. This is converted into the dibromide(3) by treatment with NBS (note that tetralin 1,2-epoxide is unstable to bromination with NBS). The... 

Tetrakis(pyridine)copper(I) perchlorate, 479-480 Tetralin, 290 Tetralin 1,2-epoxide, 458 a-Tetralone, 290, 513 (3-Tetralones, 337 Tetramethoxyethylene, 510 Tetramethylammonium bromide, 578 2,3.,6,7-Tetramethylanthracene, 15 Tetramethylbarbituric acid, 431... 

Intramolecular alkylations of epoxides at rp -centers are also possible thus treatment of the epoxyamide (173) with i-butyllithium affords moderate to good yields of the dihydiobenzofurans (174). However, the homologous system (175) is converted into the tetralin framework (176) rather than to an indan derivative, with the magnesium bromide presumably serving to activate the epoxide. Under similar conditions, the styrene oxide (177) is converted into the benzocyclobutanol (178) presumably by... 

The second method proposed by Ishii uses hydroperoxides from the in situ NHPTcatalyzed oxidation of tetralin or ethylbenzene to epoxidize olefins directly by means of Mo(CO)6 [18] (Scheme 6.2). 

Epoxidation.2 The reaction of tetralin hydroperoxide (cumene, cyclohexyl, and /-butyl hydroperoxides were also used, but to a lesser extent) with cyclohexyl metaborate (This volume)3 in the presence of an olefin results in formation of an epoxide from the olefin and generation of tetralol. The new reagent is very similar in behavior to penoxyacids. Transient hydroxonium ions, OH+, are postu-... 

EPOXIDATION m-Chloroperbenzoic acid. Hydrogen peroxide, basic. Hydrogen peroxide—Phenylisocyanate. Hydrogen peroxide-Selenium dioxide. Iodine. Peracetic acid. Perlauric acid. Tetralin hydroperoxide. Vanadium oxyacetyl-acetonate. 

Cyclohexyl metaborate activates alkyl peroxides so that the combination provides effective epoxidizing agents (52). A good arrangement of soft-hard fragments ready for transfer of an oxygen to olefins is shown. The harder phenyl metaborate reacts with the hydroxy oxygen of tetralin hydroperoxide (53). 

---