Of alcohols and phenols

Tablel.10 Retained Trivial Names of Alcohols and Phenols with Structures 1.24...

Addition of alcohols and phenols ia the presence of anhydrous hydrogen chloride gives 0-substituted pseudourea salts (17). The reaction is sluggish except with the lower alcohols, and long reaction time and temperatures up to 100°C are requited to obtain good yields. 

Substitution of chloropolymer is possible using a variety of nucleophiles. The most common are sodium salts of alcohols and phenols. Thermoplastics are obtained using a single substituent, whereas multiple substituents of sufficiently different size lead to elastomers (2). Liquid crystal behavior similar to polysHoxanes has been noted in most homopolymers. The homopolymer formed using trifluoroethanol as a substituent has received a fair amount of academic scmtiny (7). 

Selective Deprotection of Alcoholic and Phenolic TBDMS Ethers (14)... 

The reaction of alkyl sulfates with alkoxide ions is quite similar to 10-12 in mechanism and scope. Other inorganic esters can also be used. One of the most common usages of the reaction is the formation of methyl ethers of alcohols and phenols by treatment of alkoxides or aroxides with methyl sulfate. The alcohol or phenol can be methylated directly, by treatment with dimethyl sulfate and alumina in cyclohexane. Carboxylic esters sometimes give ethers when treated with alkoxides (Bal2 mechanism, p. 473) in a very similar process (see also 10-24). 

The addition of alcohols and phenols to double bonds is catalyzed by acids or bases. When the reactions are acid catalyzed, the mechanism is electrophilic, with H as the attacking species. The resulting carbocation combines with a molecule of alcohol ... 

Further examples of the reaction ROH -> RC02R are included in Section 107 (Esters from Acid Derivatives) and in Section 45 A (Protection of Alcohols and Phenols). 

This section lists examples of the hydrogenolysis of alcohols and phenols (ROH -> R-H). 

Lithium aluminium hydride Higuchi and co-workers100 introduced it as a titrant, usually in tetrahydrofuran (previously liberated from peroxide), for the titration of alcohols and phenols according to the overall reaction... 

Alternatively, the Sn2 nucleophilic substitution reaction between alcohols (phenols) and organic halides under basic conditions is the classical Williamson ether synthesis. Recently, it was found that water-soluble calix[n]arenes (n = 4, 6, 8) containing trimethylammonium groups on the upper rim (e.g., calix[4]arene 5.2) were inverse phase-transfer catalysts for alkylation of alcohols and phenols with alkyl halides in aqueous NaOH solution to give the corresponding alkylated products in good-to-high yields.56... 

Glucosidase Cleavage of p-glucosides of alcohols and phenols Cycasin, rutin... 

Several organohypervalent iodine reagents have been used for the oxidation of alcohols and phenols such as iodoxybenzene, o-iodoxybenzoic acid (IBX), bis(trifluoroa-cetoxy)iodobenzene (BTI), and Dess-Martin periodinane etc. But the use of inexpensive iodobenzene diacetate (IBD) as an oxidant, however, has not been fully exploited. Most of these reactions are conducted in high boiling DMSO or toxic acetonitrile media that results in increased burden on the environment. 

The oxidative carbonylation of alcohols and phenols to carbonates can be catalyzed by palladium or copper species [154-213]. This reaction is of particular practical importance, since it can be developed into an industrial process for the phosgene-free synthesis of dimethyl carbonate (DMC) and diphenyl carbonate (DPC), which are important industrial intermediates for the production of polycarbonates. Moreover, DMC can be used as an eco-friendly methylation and carbonylation agent [214,215]. The industrial production of DMC by oxidative carbonylation of methanol has been achieved by Enichem [216] and Ube [217]. 

Phase-transfer catalysed esterification of alcohols and phenols with acid chlorides... 

Symmetrical and unsymmetrical carbonates have also been obtained from the reaction of chloroformates with alcohols under soliddiquid conditions [55], and the reaction of carbamoyl fluorides with alcohols produces alkyl carbamates [58]. r-Butyloxycarbonylation of alcohols and phenols is effected by trans-esterification of di-r-butyl carbonate under basic phase-transfer catalysed conditions [59]. Yields tend to be high for the reaction with the phenols (>85%), but only moderate with the alcohols (30-81%). 

Atherton-Todd phosphorylation of alcohols and phenols (Table 3.22)... 

Sulphonic esters have been obtained from the sulphonyl chlorides in high yields under mild conditions for a range of alcohols and phenols [e.g. 18, 19]. Of particular value is the protection of glycosides possessing a free hydroxyl group and hydroxy-steroids, which are tosylated readily under phase-transfer conditions [20-22]. Alkyl sulphinites have been obtained in a similar manner [23]. Alternatively, preformed tetra-rt-butylammonium sulphonates or their alkali metal salts have also been alkylated with haloalkanes or alkyl fluorosulphonates [24,25]. In contrast with more classical procedures, tosylation of alcohols, which are susceptible to E/Z-isomerism, e.g. Z-alk-2-en-l-ols, occurs with retention of their stereochemistry under phase-transfer catalysis [26]. 

Glueosidase Clostridia, Eubacteria Cleavage of P-glycosidases of alcohols and phenols... 

Alcohols and phenols eonsist of two parts, an alkyl/aiyl group and a hydrojQTl group. The properties of alcohols and phenols are ehiefly due to the hydrojQTl group. The nature of alkyl and aiyl groups simply modify these properties. 

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