Oxymetallation. Part 11. Synthesis of cyclic secondary alkyl peroxides via the peroxymercuration of α,ω-dienes
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 522-530
- https://doi.org/10.1039/p19780000522
Abstract
Six cyclic peroxides of the form [graphic omitted] [X = HgCl (1), H (2), or Br (3); n= 1 (a) or 2 (b)] have been prepared in high yield via the reaction of penta-1,4-diene or hexa-1,5-diene with hydrogen peroxide and mercury(II) nitrate. The new compounds are identified by 1H and proton-decoupled 13C n.m.r. spectroscopy and additionally by mass spectrometry where X = H or Br; compound (1a) isomerises to a β-oxo-alcohol when dissolved in pyridine. The 1,2-dioxacyclopentanes are obtained as approximately equimolar mixtures of cis-and trans-isomers whereas the 1,2-dioxacyclohexanes contain about three times as much trans- as cis-isomer. The configurations are assigned on the basis of 13C and 1H n.m.r. chemical shifts and variable-temperature n.m.r. spectra.Keywords
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