Q7(e). Lead tetraacetate cyclization of butanol
Explain the conversion of n-butanol into tetrahydrofuran with Pb(OAc)₄ in benzene, on heating or irradiation.
Answer in brief
An alkoxy radical undergoes intramolecular 1,5-H transfer; oxidation and ring closure give tetrahydrofuran.
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Coverslead tetraacetatealkoxy radical1,5-hydrogen transfertetrahydrofuran synthesisremote functionalization
All parts of Question 7
- 7(a) Woodward–Fieser calculations10 marks
- 7(b) Tautomers and chromophores5 marks
- 7(c) ESR of pyrazine5 marks
- 7(d) Infrared distinctions10 marks
- 7(e) Lead tetraacetate cyclization of butanol10 marks