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Steric and electronic effects in the synthesis of biaryls and their heterocyclic congeners using intramolecular free radical [1,5] ipso substitution reactions

✍ Scribed by Maria Lucília E.N da Mata; William B Motherwell; Feroze Ujjainwalla

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
233 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Hindered biaryls and heterobiaryls are even easier to prepare by intramolecular free radical [1,5] ipso substition using sulfonamide and sulfonate tethering chains, since the introduction of either electron releasing or electron withdrawing groups ortho to the sulfonyl substituted acceptor ring facilitates the overall reaction.

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ChemInform Abstract: Steric and Electron
ChemInform Abstract: Steric and Electronic Effects in the Synthesis of Biaryls and Their Heterocyclic Congeners Using Intramolecular Free Radical (1,5) ipso Substitution Reactions.
✍ M. L. E. N. DA MATA; W. B. MOTHERWELL; F. UJJAINWALLA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 2 views

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Observations on the nature of the tether
Observations on the nature of the tethering chain in the synthesis of biaryls and heterobiaryls via intramolecular free radical ipso substitution reactions
✍ Maria Lucília E.N. da Mata; William B. Motherwell; Feroze Ujjainwalla 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 223 KB

A study of benzylic sulfonates and their corresponding N-methylsulphonamide derivatives as substrates in potential free radical [1,6] ipso substitution reactions reveals a preference for the alternative [1,7] addition mode. Empirical guidelines for biaryl and heterobia~l synthesis using this approac