Journal of the Chemical Society. Perkin transactions I p. 2951 - 2955 (1990)
Update date:2022-08-02
Topics:
Bloodworth, A. J.
Courtneidge, J. L.
Curtis, Richard J.
Spencer, Michael D.
Unsaturated hydroperoxides (R1R2CHO2H), 2-phenylpent-4-enyl hydroperoxide (1), 3-phenylhex-5-en-2-yl hydroperoxide (2), 5-methylhex-5-en-2-yl hydroperoxide (3), cyclo-oct-4-enyl hydroperoxide (18), and cyclo-oct-3-enyl hydroperoxide (24) have each been prepared from the corresponding carbonyl compound (R1R2CO) by the sequence: i, conversion to the p-tosylhydrazone (R1R2C=N-NHTs); ii, reduction with sodium cyanoborohydride at pH 3.5 to give the N'-p-tosylhydrazine (R1R2CH-NH-NHTs); and iii, oxidation with hydrogen peroxide and sodium peroxide.Isomerisation occurs in the preparation of the cyclo-octenyl hydroperoxides, particuarly if the pH falls markedly below 3.5 in the reduction step.
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