Reduction glycol cleavage

As to the first point, tartronic dialdehyde (8) could, as has already been suggested (32), be oxidized by classical glycol cleavage to give three molar equivalents of formic acid (and no carbon dioxide) with the concomitant reduction of two (instead of three for the enol form) molar equivalents of periodate ... 

Thermal Stability. Dimethyl sulfoxide decomposes slowly at 189°C to a mixture of products that includes methanetliiol. formaldehyde, water, bis(methyhhio)methane, dimethyl disulfide, dimethyl sulfone, and dimethyl sulfide. The decomposition is accelerated by acids, glycols, or amides. Sulfoxides undergo oxidation, reduction, carbonsulfide cleavage, and Pttmmerer reactions. 

Conversion of the cryrtro-aldols to eryrAro-a-inethyl-/J-hydroxy aldehydes is effected by reduction with LiAlH4 to a mixture of isomeric diols followed by glycol cleavage by sodium periodate in aqueous methanol.3... 

P2i2i2j Z = 4 D = 1.46 R = 0.105 for 961 intensities (film measurements). Compound obtained by glycol cleavage of methyl 6-O-trityl-a-D-glucopyranoside, followed by reduction, sulfonylation, and ring-closure by sulfide anion. The 1,4-oxathiane ring has a distorted chair conformation, with the sulfoxide bond equatorial and the bond to the methoxyl group axial. 

Regioselectivity of C—C double bond formation can also be achieved in the reductiv or oxidative elimination of two functional groups from adjacent carbon atoms. Well estab llshed methods in synthesis include the reductive cleavage of cyclic thionocarbonates derivec from glycols (E.J. Corey, 1968 C W. Hartmann, 1972), the reduction of epoxides with Zn/Nal or of dihalides with metals, organometallic compounds, or Nal/acetone (seep.lS6f), and the oxidative decarboxylation of 1,2-dicarboxylic acids (C.A. Grob, 1958 S. Masamune, 1966 R.A. Sheldon, 1972) or their r-butyl peresters (E.N. Cain, 1969). 

A classical method for the vicinal hydroxylation of a double bond involves treatment with osmium tetroxide to give a cyclic ester, followed by reductive cleavage to the glycol ... 

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