Organic Lab Reactions 278

Organic Lab Reactions 278 - NATURE OF THE At-COHOL 273 of...

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NATURE OF THE At-COHOL 273 of the nitro group 49> 80 with the formation of l-chloro-2-naphthalenedia- zonium chloride. Here again, diazotization with sulfuric acid prevents the lose of the nitro group. 61 The use of diazo nitrates instead of the acid sulfates offers no advan- tage and may result in nitrated products. 25 Deamination of large quantities of 2-nitro-3'-bromobenzidine by the sulfuric acid procedure proves tedious. A convenient method involves preparation of the dry bisdiazofluoborate and decomposition in absolute ethyl alcohol. The yield of pure product is 78%, a 26% increase over that obtained by employing the tetrazonium acid sulfate. 62 NO 8 Br H 2 N— i . \—i \— NH 2 -* NO 2 Br BF«-N,+-f V-f . V-N a +BF 4 - Nature of the Alcohol All alcohols do not produce the same result with a given diazonium salt. The use of methanol greatly increases the probability that ethers will be formed. For example, if the tetrazonium chloride derived from benzidine is treated with absolute ethyl alcohol, biphenyl is obtained in
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