Ethylene derivs., cyclic diols

Cleavage of ethylene derivs. to alcohols and amines Diols and diamines from cyclic ethylene derivs. 

Ozone/sodium tetrahydridohorate Diols by oxidative ring opening of cyclic ethylene derivatives via a-hydroxy-a -alkoxyperoxides Retention of carboxyl groups... 

Diols that bear two hydroxyl groups m a 1 2 or 1 3 relationship to each other yield cyclic acetals on reaction with either aldehydes or ketones The five membered cyclic acetals derived from ethylene glycol (12 ethanediol) are the most commonly encoun tered examples Often the position of equilibrium is made more favorable by removing the water formed m the reaction by azeotropic distillation with benzene or toluene... 

In a similar combination of insertions of C=S into Sn—O bonds, and elimination of (Bu3Sn)2S, bis(tributyltin) derivatives of 1,2-diols react with CS2 to give first the corresponding cyclic ethylene thionocarbonate, and then the spiro-orthocarbonate . 

Ethylene sulfite also reacts with chlorine gas under photochemical conditions to form 2-chloroethyl chlorosulfite CICH2CH2OSOCI in excellent yield [67JCS(C)314], Some anomalous results were reported in the reaction of ethylene sulfite to furnish fluoroethanol, but they could not be substantiated (83M11). Tewson attempted to carry out nucleophilic opening of a cyclic sulfite derived from a sugar with tetrabutylammonium fluoride, which led to the hydrolysis of cyclic sulfite to furnish the corresponding diol (83JOC3507). 

Cyclic Acetals Formation of an acetal using a diol as the alcohol gives a cyclic acetal Cyclic acetals often have more favorable equilibrium constants, since there is a smaller entropy loss when two molecules (a ketone and a diol) condense than when three molecules (a ketone and two molecules of an alcohol) condense. Ethylene glycol is often used to make cyclic acetals its acetals are called ethylene acetals (or ethylene ketals). Dithiane (Section 18-8) and its alkylated derivatives are examples of cyclic thioacetals (sulfur acetals). 

The pioneering work carried out in Moore s laboratory in the 1970s and 1980s represents the first systematic approach to furan polyesters (after numerous isolated and rather qualitative publications on the topic), which were prepared fi om 2,5-furandicarboxylic derivatives in conjunction with aliphatic, furanic and tetrahydrofuranic diols as well as with bisphe-nol A [4d, 4e]. In the same period, the furan hydroxyacid 10 was polymerized to give both linear and cyclic oligomers at relatively low temperatures, but its condensation with ethylene glycol produced black intractable resins [4d, 38]. 

Heating 1,4,5,6-tetra-O-benzyl-myo-inositol with ethylene carbonate and a trace of sodium bicarbonate affords the 2,3-cyclic carbonate derivative. The reaction fails where there is a trans-diol arrangement as with 1,2,3,6-tetra-O-benzyl-myo-inositol. ... 

Corey and Hase have found that 1,3-dithiolans and 1,3-dithians can be converted in good yields into dimethyl acetals, cyclic acetals, or thioacetals (or thioketals) upon reaction of the mono-5-methylated derivatives with methanol, ethylene glycol, and mercaptoethanol, respectively. These interchanges do not appear to involve the free carbonyl compound. The disulphonium salt prepared by the reaction of triethyloxonium tetrafluoroborate with 2-phenyl-l,3-dithiolan can be used to prepare benzylidene derivatives of 1,2-, 1,3-, and 1,4-diols (30— 80%) under basic conditions. This reaction appears to have considerable potential as a route to benzylidenated sugars. 

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