Organic Lab Reactions 240

Organic Lab Reactions 240 - phenyl and from...

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TERPHENYLS AND DERIVATIVES 235 Fluorenonecarboxylic acids are accessible from the products formed by coupling diazotized esters of methyl 3-aminophthalic acids with benzene and benzene derivatives. From diazotized methyl 3-aminophthalate and benzene, methyl 3-phenylphthalate (IX) is obtained in 35% yield. COOCH3 COOCH 3 Terphenyls and Derivatives. p-Terphenyl can be prepared satisfac- torily in two ways: (a) from the nitrosoacetyl derivative of 4-aminobi- phenyl, and (b) from the 6is-nitrosoacetyl derivative of p-phenylenedi- amine. The yields by both routes are about the same (50-60%). I(NO)COCH, + CH 3 C0(N0)N- -N(NO)COCH S + m-Terphenyl can be prepared by analogous reactions from 3-aminobi-
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Unformatted text preview: phenyl and from m-phenylenediamine; the preparation of o-terphenyl by these methods has not been reported. Derivatives of m-terphenyl and p-terphenyl can be prepared from the substituted aminobiphenyls. When the diacetyl derivative of 3-nitro-l,4-phenylenediamine was treated with nitrous fumes, only a mononitroso derivative was formed, for the prod-uct obtained by treating the nitroso compound with benzene was 3-nitro-4-acetamidobiphenyl (X; 32% yield); the acetamido group ortho to the nitro group was not nitrosated. By coupling the bis-nitrosoacetyl deriva-tive of benzidine with ben/ene, quaterphenyl (XI) is obtained in 17% yield. CH3CONH...
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