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1980•Journal of the Chemical Society Chemical CommunicationsRequires access

Solvolysis of 2-adamantyl ONN-azoxytoluene-p-sulphonate. A new reaction

Howard Maskill, Peter Murray‐Rust, John T. Thompson, Alan A. Wilson

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Abstract

The first secondary alkyl azoxyarenesulphonate, 2-adamantyl azoxytosylate, has been made and shown to have the Z configuration about the nitrogen–nitrogen double bond; rates of solvolysis and activation parameters in aqueous ethanol, aqueous trifluoroethanol, and aqueous hexafluoropropan-2-ol have been determined and a solvolytic mechanism involving unimolecular fragmentation and carbonium ion intermediates is proposed.

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What this paper is about

The first secondary alkyl azoxyarenesulphonate, 2-adamantyl azoxytosylate, has been made and shown to have the Z configuration about the nitrogen–nitrogen double bond; rates of solvolysis and activation parameters in aqueous ethanol, aqueous trifluoroethanol, and aqueous hexafluoropropan-2-ol have been determined and a solvolytic mechanism involving unimolecular fragmentation and carbonium ion intermediates is proposed.

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OpenAlex reports 4 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

The first secondary alkyl azoxyarenesulphonate, 2-adamantyl azoxytosylate, has been made and shown to have the Z configuration about the nitrogen–nitrogen double bond; rates of solvolysis and activation parameters in aqueous ethanol, aqueous trifluoroethanol, and aqueous hexafluoropropan-2-ol have been determined and a solvolytic mechanism involving unimolecular fragmentation and carbonium ion intermediates is proposed.

Key concepts: Solvolysis, Carbonium ion, Chemistry, Aqueous solution, Fragmentation (computing), Alkyl, Ethanol, Nitrogen

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Solvolysis of 2-adamantyl ONN-azoxytoluene-p-sulphonate. A new reaction — Research Paper | ScholarLens