Studies on the rearrangement of 1- and 2-naphthylsulphamic acids

WILLIAM J. SPILLANE

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Abstract

The rearrangement of sodium 1-naphthylsulphamate in dioxan-sulphuric acid gives 1-aminonaphthalene-4-sulphonic acid as the main product. 1-Aminonaphthalene-2-sulphonic acid is not formed under the conditions used for the rearrangement. Studies with [35S]sulphuric acid and sodium 1-naphthyl[35S]sulphamate indicate that the rearrangement is partly intramolecular in dioxan-sulphuric acid. Mechanisms for both the inter- and intra-molecular paths are presented. Sodium 2-naphthylsulphamate does not rearrange under these conditions nor does it rearrange under conditions previously reported as being suitable for its rearrangement.

Original languageEnglish (Ireland)
Pages (from-to)2409-2414
Number of pages6
JournalJournal Of The Chemical Society B: Physical Organic
Publication statusPublished - 1 Jan 1971

Authors (Note for portal: view the doc link for the full list of authors)

  • Authors
  • Spillane,W.J.,Scott, F.L.,Goggin, C.B.

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