Hydrolysis of 1,4,6-trioxaspiro[4.5]decanes to .delta.-lactones using 2,3-dichloro-5,6-dicyanobenzoquinone in aqueous acetone

Oxidation of Alcohols to Aldehydes and Ketones

“…126 Acetic acid, 127 pyridinium triXuoroacetate (PTFA) 121 or pyridinium tosylate (PPTS) 128 are often added in order to speed up PDC oxidations. Apparently, this acceleration is unrelated with its water-scavenging nature, although best results are obtained when thoroughly activated material is used.…”

“…127 Orthoesters are hydrolyzed on contact with DDQ via a mechanism in which apparently the acidity of the DDQ hydroquinone plays no role. 128 O Ref. 128 O Ref.…”

“…Interestingly, it is possible either to hydrolyze an orthoester in the presence of an unsaturated alcohol, using wet acetone as solvent, or oxidize an unsaturated alcohol in the presence of an orthoester, employing anhydrous benzene as solvent. 128 Treatment of compound 95 with DDQ produces the hydrolysis of the orthoester when wet acetone is used as solvent and the oxidation of the allylic alcohol when dry benzene is employed. 128 Treatment of compound 95 with DDQ produces the hydrolysis of the orthoester when wet acetone is used as solvent and the oxidation of the allylic alcohol when dry benzene is employed.…”