From diols

Treatment of cyclic thionocarbonate (36) derived from 1,3-diol, with the Bu3 SnH/AIBN system generates the corresponding monodeoxygenated product (37), as... 

The alkyloxyphosphonium fluorides are prepared from 1,3-diols in a two-step procedure." None of these methods has found broad application thus far. 

Dioxanes are prepared from 1,3-diols and either an aldehyde. - a ketone, " an acetal, or mcthoxyniethyl chloride. 4-Tolucnesulfonic acid is the catalyst ofchoice, - - e g. diol 9 reacts with isobutyraldchyde to give the cyclic acetal 10. For the intramolecular transacetalization of bis(methoxymethyl)-protccted diol 11 to dioxane 12, Amberlyst-15 (beaded polyslyrcnesulfonic acid) is needed. ... 

Wharton fragmentation Base-induced formation of medium-sized cyclic alkenes from 1,3-diol monosulfonates. 480... 

The oxetans (41a) and (41b) have been shown to be the products of the reaction of benzaldehyde and hexamethylDewarbenzene. An efficient one-pot synthesis of oxetan from 1,3-diols has been developed this year. ... 

Alcohols with a nucleofuge leaving group in the r-position can be cyclized to give oxetanes. Thus the cyclodehydrohalogenation of halo alcohols occurs in an analogous way to the oxirane synthesis from y -halogenated alcohols (see p 20). Oxetanes can be prepared from 1,3-diols via monoarene sulfonates ... 

Hermans 28) and later other workers 61) showed that boric esters are formed more readily from 1,3-diols than from 1,2-diols. Early stereo-... 

Transesterification of boronic acid esters s. 44, 52 2-Amino-1,3-dioxanes from 1,3-diols s. 44, 941... 

Formoxy-3-ethylenes from 1,3-diols via 2-amino-l,3-dioxanes G... 

Sulfite/sodium hydroxide Alcohols from 1,3-diols... 

Because of the thermodynamic stability of the ring, 1,3-dioxanes derived from aldehydes are formed more easily from 1,3-diols than 1,3-dioxolanes from 1,2-diols [7]. Substituents may affect the yield of the cyclic acetals. In a ruthenium-catalyzed reaction, an increase of yields was noted in the following order depending on the diol used (Figure 5.14) [8]. Glycerol usually gives mixtures of five- and six-membered acetals. 

Gassman et al have published full details of their work on the synthesis of fused cyclopropanes by reaction of l-chloro-2-alkylcycloalkenes with organo-lithium reagents (see Vol. 4, p. 244), and further aspects of the synthesis of cyclopropanes from 1,3-diols using McMurry s reagent have been reported. ... 

Sulfur trioxide-pyridinejdimethyl sulfoxide a,/ - thyleneoxo compds. from 1,3-diol monoesters... 

Scheme 10 Synthesis of six-membered cyclic carbonates from 1,3-diols and diethyl carbonate.

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