Alcohols, hydroxy

Naphthyl)ethyl isocyanate 2 for chromatographic resolution of alcohols, hydroxy esters thiols via diastereomenc derivatives. 

One of the most useful ways of introducing fluorine into organic compounds is the placement of the hydroxyl group in alcohols hydroxy compounds, and carboxylic acids Methyl alcohol reacts with anhydrous hydrogen fluoride at 100 500 °C in the presence of aluminum fluoride [60, 61], zinc fluoride [62] chromium fluonde [63], or a mixture of aluminum and chromium fluondes [64] to give a 20-78% yield of fluoromethane Attempted fluorinations of higher alcohols by this method failed [60]... 

Monosaccharides in which an alcoholic hydroxy group has been replaced by a hydrogen atom are called deoxy sugars (see 2-Carb-13). 

Substituents replacing the hydrogen atom of an alcoholic hydroxy group of a saccharide or saccharide derivative are denoted as O-substituents. The 0- locant is not repeated for multiple replacements by the same atom or group. Number locants are used as necessary to specify the positions of substituents they are not required for compounds fully substituted by identical groups. Alternative periphrase names for esters, ethers, etc. may be useful for indexing purposes. For cyclic acetals see 2-Carb-28. 

A disaccharide in which one glycosyl unit has replaced the hydrogen atom of an alcoholic hydroxy group of the other is named as a glycosylglycose. The locants of the glycosidic linkage and the anomeric descriptor(s) must be given in the full name. 

Quinone methides play an important role in lignification. They are produced directly, as intermediates, when lignin monomers, be they hydroxycinnamyl alcohols, hydroxy-cinnamaldehydes, or hydroxycinnamates, couple or cross-couple at their 8- positions. A variety of postcoupling quinone methide rearomatization reactions leads to an array of structures in the complex lignin polymer (Fig. 12.2). 

Table 9.1 Enzyme-catalysed stereoselective reduction of diketones/keto esters to keto alcohols/hydroxy esters...

Class 1 Liqnids capable of forming three-dimensional networks of strong hydrogen bonds, e.g., water, poly- and amino-alcohols, hydroxy-acids, etc. 

When electronegative substituents are present, oxadiazoles undergo nucleophilic reactions on the carbon atoms, both in position 3 or 5- The substitution of halogen, alkoxy and trichloromethyl derivatives has. been studied. 5-Halogeno-oxadiazoles react with ahphatic and aromatic primary and secondary amines, to give the corresponding amino-derivatives. With sodium hydroxide and -alcoholate, hydroxy and alkoxy oxadiazoles are obtained 25 a, 55 b). 

The alkylation of metalated imines, hydrazones, 4,5-dihydrooxazoles, 4,5-dihydroisoxazoles, 5,6-dihydro-4/7-1,2-oxazines and 2,5-dialkoxy-3,6-dihydropyrazines (i.e., azaenolates) is a commonly used method in asymmetric synthesis of enantiomerically enriched aldehydes, ketones, spiroacetals, amines, /J-oxo esters, carboxylic acids, lactones, 1,3-amino alcohols, /(-hydroxy ketones and amino acids. 

Synonyms Allyl alcohol oxide epihydrin alcohol l,2-epoxy-3-hydroxypropane 2,3-epoxy-l-propanol ( )-2,3-epoxy-1-propanol glycide ( )-glycidol (RS)-glycidol dl-glycidol glycidyl alcohol hydroxy-l,2-epoxypropane l-hydroxy-2,3-epoxypropane 2-(hydroxymethyl)oxirane 3-hydroxypropylene oxide oxiranyl-methanol racemic glycidol... 

Alcohols Carboxylic acids Phenols Primary and secondary amines Oximes Nitro compounds (with a-H atoms) Nitriles (with a-H atoms) Polyhydroxyalcohols Amino alcohols Hydroxy acids Polyprotic acids Polyphenols... 

B. R. Castro, Replacement of alcoholic hydroxy groups by halogens and other nucleophiles via oxyphosphonium intermediates, Org. React. 29 1 (1983). 

Intermolecular and intramolecular nucleophilic substitution of an alcoholic hydroxy group by the triphenylphosphine/dialkyl azodicarboxylate redox system is widely used in the synthesis and transformation of natural products and is known in organic chemistry as the Mitsunobu reaction.1951 This reaction starts with formation of the zwitterionic phosphonium adduct 19 (Scheme 9) from triphenylphosphine and diethyl (or diisopropyl) azodicarbox-... 

Reetz et alJ33 described the stereoselective synthesis of partially protected a-hydroxy-y-amino acids 8 (Scheme 6) as potential pseudo-y-tum mimetics. X-ray diffraction structure analysis as well as NMR studies in CDC13 showed that these compounds display a pseu-docyclic eight-membered ring arising from an intramolecular H-bond between the amide carbonyl (i -1) and the alcohol hydroxy group (i). However, the ability of such a H-bond to induce or stabilize a pseudo-y-turn structure in an aqueous environment is doubtful. 

GLYCOL. A dihydric alcohol (i.e.. a compound conlaining two alcoholic hydroxy] groups). The chemical properties are represented by those of the simplest members of the class, ethylene glycol, 1,2-ethanediol. CH-OH CHjOH. which is a colorless, viscous liquid, of sweetish taste. Odorless, boiling point I97°C. miscible in all proportions with water or alcohol, slightly soluble in ether. Like ethyl alcohol, ethylene glycol is often called by the class name. 

This technique allows one to convert phenolic and alcoholic hydroxy-substituted compounds present in the various oxidation mixtures directly... 

If the halohydrins were added to solutions containing C206"2 or COl, or HCOj anions in the presence of tetra-alkylammonium cations, then CCs would have been obtained in good to high yields. Thus, the formation of CCs was seen to require the presence of a suitable leaving group in an a position with respect to the alcoholic hydroxy group (e.g., halohydrins) [194],... 

NX - BENZYL ALCOHOL, -HYDROXY-alpha-( (METHYLAMINO)METHYL >-, HYDROCHLORIDE, (-)-... 

B. R Castro, Replacement of Alcoholic Hydroxy Groups by Halogens and Other Nucleophiles via Oxyphosphonium Intermediates, Org. React. 1983, 29, 1-162. 

LiInH4 is increased by the introduction of phenyl group(s) LiPhInH3 and LiPh2InH2 readily reduce aldehydes, ketones, acid chlorides, and even esters to the corresponding alcohols. Hydroxy ketones and diketones are reduced with lithium indium hydride to give meso-diols selectively. a-Hydroxy ketones and a-diketones are reduced to meso-1,2-diols with high diastereoselectivities, whereas the selectivities of /3-hydroxyketones and /3-diketones are less satisfactory.365... 

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