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- Title
Functionalization of naphthalene: a novel synthetic route to brominated naphthoquinones.
- Authors
Cakmak, Osman; Akar, Kiymet Berkil; Kaplan, Nuri
- Abstract
An efficient procedure is described for synthesis of 2,5,8-tribromonaphthoquinone (12) from naphthalene in four reaction steps. Silver-promoted solvolysis of hexabromide 3 produces the specific diastereostereoisomer 10. Dehydrobromination of 10 using sodium methoxide gives tribromodihydronaphthalene-1,4-diol 11 in high yield. PCC oxidation of either 10 or 11 results in the formation of 2,5,8-tribromonaphthalene-1,4-dione (12).
- Subjects
NAPHTHALENE; NAPHTHOQUINONE; RING formation (Chemistry); DEHYDROBROMINATION; SODIUM compounds; STEREOISOMERS; ORGANIC synthesis; OXIDATION
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2012, p274
- ISSN
1551-7004
- Publication type
Article