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31.5.1.5.8 Method 8: Synthesis from Cyclohexene Oxides

DOI: 10.1055/sos-SD-031-00299

Thomas, A. W.Science of Synthesis, (200731387.

The simplest of all arene oxides, 7-oxabicyclo[4.1.0]hepta-2,4-diene (245), reacts with 20mol% of tetracarbonyldi-μ-chlorodirhodium(I) dimer in chloroform to give a 1:1 mixture of benzene and phenol. However, when methanol is employed as the solvent a 2:1 mixture of benzene and phenol is formed. In the same way 1a,7b-dihydronaphtho[1,2-b]oxirene (246) affords 1-naphthol in 89% yield, and 1a,9b-dihydrophenanthro[9,10-b]oxirene (247) gives phenanthren-9-ol in 82% yield (Scheme 91).[‌177‌]

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