Aliphatic and alicyclic alcohols

This procedure has been used successfully for conversion of various aliphatic and alicyclic alcohols to the corresponding iodides. Yields of iodides from 1-propanol, 2-methyl-1-propanol, 2-methyl-2-propanol, and cyclohexanol were 95, 88, 90, and 79.5%, respectively. 

Ipatieff et al. studied the hydrogenolysis of various aliphatic and alicyclic alcohols in the presence of a Ni-Al203 catalyst at 210-225°C and 10 MPa H2.304 3,3-Dimethyl-1-butanol yielded a mixture of 2,2-dimethylbutane and neopentane as the main products, while in the presence of either Ni-kieselguhr or Raney Ni, neopentane was formed in > 95% yields (eq. 13.161). 

Methyl ethers of aliphatic and alicyclic alcohols are also cleaved with Lewis acids and in Scheme 1,4 we showed a methyl ether deprotection in a synthesis... 

Under these conditions saturated primary and secondary aliphatic and alicyclic alcohols are recovered essentially unchanged. This selectivity was illustrated impressively by conversion of Z-3-methyl-2-pentene-l,5-diol (4) by treatment with the complex (I) in methylene chloride briefly at - 20° and then at 0° for 1 hr. into the allylic monochloride (5), isolated in 87% yield. 

A broad variety of substrates were efficiently glycosylated by glycosidases such as aliphatic and alicyclic alcohols [14], phenols, oximes, steroids and terpenes [15], amino acids [16], alkaloids [17] and many other substances. 

Doddrell et al. (80, 66) have examined the angular dependence of V(C-C) in a number of aliphatic and alicyclic alcohols. In contrast to the carboxylic acids, 37(C-C) is observed to be a maximum, 5-4 Hz, for a dihedral angle near 0°. For the trans arrangement, — 180°, 3/(C-C) is 3-2 Hz. At dihedral angles of 90 and 270°, 3/(C-C) is less than 0-4 Hz. Observed 3/(C-C) values for the alcohols and carboxylic acids (66, 80, 52) have been compared with values calculated (INDO-FPT) for the model compounds butane, 2-butanol, and butanoic acid. The calculated coupling constants are given in Table V. (80) Also, experimental and calculated 3J(C-C) values for the carboxylic acids are shown in Fig. 2. The calculations, which assumed only the Fermi contact... 

Gracza, L. and Ruff, P. (1986) Uber die hoheren Alkohole von Piperis methystici rhizoma Aliphatic and alicyclic alcohols of Piperis methystici rhizoma. Archive der Pharmazie, 319, TTS-All. 

Radicofunctional nomenclature is no longer used except for simple aliphatic and alicyclic alcohols, e.g. methyl, pentyl, cyclohexyl alcohol, etc., and could be dispensed with here too. 

The concept of a group is especially important in organic chemistry. A functional group represents a set of atoms that is closely linked with chemical reactivity and defined classes of substances. For instance, the functional group hydroxyl, -OH, is characteristic of the classes alcohol, phenol and enol. Alcohols are often represented by the general formula R-OH, in which R- represents a hydrocarbon group typical of aliphatic and alicyclic substances. 

Further examples of reactions of aliphatic and alicyclic polycarboxylic acids with sulfur ictra-fluoride or sulfur tetrafluoride/hydrogen fluoride are known.The reaction of aliphatic hydroxycarboxylic acids with sulfur tetrafluoride can give different products depending on the reaction conditions, the position of the hydroxy group, and the presence of other substituents. The main products from a-hydroxycarboxylic acids are trifluoroalkyl fluorosulfites, e.g. 19, which can be hydrolyzed quantitatively to the corresponding alcohols. ... 

Although aliphatic and alicyclic hydrocarbons react with most sul-fonating agents, the reactions are not suitable for the preparation of the pure sulfonic acids. " Certain olefins react with sulfur dioxide-dloxane complex to give olefinic sulfonic acids In this way, cyclohexene is converted to l-cyclohexene-3-sulfonic acid, whereas with concentrated sulfuric acid in a mixture of acetic acid and acetic anhydride the main product is 2-hydroxycyclohexanesuIfonic acld. 1-Propene-l-sulfonic acid is obtained in low yield by the action of oleum on n- or isopxopyl alcohol. ... 

There is now general agreement that Vilsmeier reactions with acetals, ketals, and the corresponding thio derivatives proceed by loss of a molecule of alcohol or thiol to give the reactive unsaturated ether or thioether with cyclic ketals the alcohol remains tethered, and may be chlorinated. The acetals and ketals are often more readily available than the unsaturated ethers, and yields of products are similar. A wide range of aliphatic and alicyclic acetals and ketals has been formylated the reaction can tolerate bulky groups at either end of the double bond, as is shown for compound 64 (Eq. 51). Products are isolated as iminium sails... 

Alcohols are rarely reduced by lithium aluminum hydride the reaction occurs only in exceptional cases, such as that of benzyl alcohols containing an amino or methoxy group ortho or para to the CH2OH group.356 However, aliphatic and alicyclic sulfonic esters are more482 or less easily483 reduced by this reagent. 

Low molecular weight products from the alkaline degradation of cellulose have been identified by g.e.-m.s. of their trifluoroacetate derivatives. Both the residual aqueous phase and the floating oily product were examined and found to contain essentially the same products. These included unsaturated, aliphatic and alicyclic hydrocarbons, aldehydes, ketones, alcohols, and furans. The synthesis of molecules with more than six carbon atoms also occurred. 

The non-polar components of waxes can be isolated also as compound classes by adsorption TLC and analysed in a subsequent gas chromatographic procedure these are long-chain hydrocarbons and esters of fatty acids with aliphatic or alicyclic alcohols [2, 149]. 

Homolipids, which consist of fatty acids linked to various alcohols, are now categorised exclusively by the structure of the bound alcohol. The most common alcohol in natural lipids is glycerol. Rarely occurring alcohols are glycols, higher monohydric aliphatic alcohols, aliphatic and alicyclic terpenoid hydroxy compounds, such as xanthophylls (see Section 9.9.1.2), and various steroid compounds (see Section 3.7.4). 

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