Alcohols carbonyl chloride fluoride

The conversion of alcohols to the corresponding alkyl fluorides by the pyridine or boron trifluoride catalyzed decomposition of alkyl fluoroformates formed by the addition of 2, or of carbonyl chloride fluoride, to alcohols has been reported.47,48... 

Fluoride ion is effective in promoting the reduction of aldehydes by organosil-icon hydrides (Eq. 161). The source of fluoride ion is important to the efficiency of reduction. Triethylsilane reduces benzaldehyde to triethylbenzyloxysilane in 36% yield within 10-12 hours in anhydrous acetonitrile solvent at room temperature when tetraethylammonium fluoride (TEAF) is used as the fluoride ion source and in 96% yield when cesium fluoride is used.83 The carbonyl functions of both p-anisaldehyde and cinnamaldehyde are reduced under similar conditions. Potassium bromide or chloride, or tetramethylammonium bromide or chloride are not effective at promoting similar behavior under these reaction conditions.83 Moderate yields of alcohols are obtained by the KF-catalyzed PMHS, (EtO SiH, or Me(EtO)2SiH reduction of aldehydes.80,83,79... 

An important general method for preparing indoles involves the catalytic elimination of ammonia from phenylhydrazones of carbonyl compounds having an a-roethylene group. Catalysts include zinc chloride, cuprous chloride, boron fluoride etherate, dilute sulfuric acid, alcoholic hydrochloric acid, and glacial acetic acid. ... 

Particularly important is the reaction of (TMS)allene with aldehydes and ketones, which provides a convenient route to secondary and tertiary homopropargylic alcohols, respectively. Treatment of (1) (1.1-1.5 equiv) with a mixture of carbonyl compound and 1.1-1.5 equiv of titanium(IV) chloride in methylene chloride produces mixtures of homopropargylic alcohols and (trimethyl-silyljvinyl chlorides. Exposure of the crude reaction product to 2.5 equiv of potassium fluoride in DMSO then furnishes the desired homopropargylic alcohols (eq 4). ... 

Detection of certain types of compounds (for example, of an aromatic skeleton). If the compound trasmits radiation (b < 1) between 220 and 800 nm, it may well be an aliphatic or alicyclic hydrocarbon, amine, nitrile, alcohol, ether, alkyl chloride, or alkyl fluoride, but the presence of conjugated double bonds, the carbonyl group, nitro group, bromine, or iodine is excluded. The detection of the aromatic nucleus in an unknown sample is carried out by measuring the absorption in the ultraviolet region of ethanolic, cyclohexane, or /i-hexane solutions of various concentrations (10 -10 mole/liter). 

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