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A common diol reaction to produce a cyclic ether. 1,2-diols and 1,3-diols can be protected using a protecting group. [13] Protecting groups are used so that the functional group does not react to future reactions. Benzylidene groups are used to protect 1,3-diols. [13]
Particularly common spiro compounds are ketal (acetal) formed by condensation of cyclic ketones and diols and dithiols. [15] [16] [17] A simple case is the acetal 1,4-dioxaspiro[4.5]decane from cyclohexanone and glycol. Cases of such ketals and dithioketals are common.
Like BPA, CBDO is a diol with a structure suitable for making polyesters. CBDO’s C 4 ring is sufficiently rigid to prevent the two OH groups from forming cyclic structures. Unlike BPA, there is no current evidence of carcinogenic or toxic effects from CBDO-based consumer products.
In cyclic systems, the reaction presents more features of interest. In these reactions, the stereochemistry of the diol plays a crucial role in deciding the major product. An alkyl group which is situated trans- to the leaving –OH group may migrate to the carbocation center, but cis- alkyl groups migrate at a very low rate.
General structure of a 1,2-acetonide. The diol is shown in blue, the acetone part in red. In organic chemistry, an acetonide is the functional group composed of the cyclic ketal of a diol with acetone. The more systematic name for this structure is an isopropylidene ketal. Acetonide is a common protecting group for 1,2- and 1,3-diols. [1]
Two mechanisms are proposed for the Criegee oxidation, depending on the configuration of the diol. [6] [7] If the oxygen atoms of the two hydroxy groups are conformationally close enough to form a five-membered ring with the lead atom, the reaction occurs via a cyclic intermediate.
A [3+2]-cycloaddition with the alkene (3) gives the cyclic intermediate 4. [ 9 ] [ 10 ] Basic hydrolysis liberates the diol ( 5 ) and the reduced osmate ( 6 ). Methanesulfonamide (CH 3 SO 2 NH 2 ) has been identified as a catalyst to accelerate this step of the catalytic cycle and if frequently used as an additive to allow non-terminal alkene ...
They are named using suffixes -diol, -triol, etc., following a list of the position numbers of the hydroxyl groups, as in propane-1,2-diol for CH 3 CH(OH)CH 2 OH (propylene glycol). Example alcohols and representations