Alcohols as starting materials

An appropriate synthesis based on alcohols as starting materials is... 

It has been reported by Matsugi et al. that PE-fo-PMMA can be synthesized by ATRP techniques with a CuBr and an N,N,N/,N//,N//-pentamethyldiethyl-enetriamine (PMDETA) catalyst system, or with a RuCl2(PPh3)3 and dibuty-lamine catalyst system. They have used terminally hydroxylated PE, produced by the metallocene-catalyzed polymerization of ethylene with allyl alcohol as starting material. The PE macroinitiator was converted to terminally bromi-nated PE by the bromination of obtained PE-OH with bromo-isobutyric bromide (Fig. 11) [67]. 

Since alkyl halides are made from alcohols by treatment with reagents such as PBr3 or HC1 and a Lewis acid, it may make sense in designing the synthesis of ethers to write the two alcohols as starting materials and decide later which to convert into an electrophile. For ether 24 the two alcohols would be 27 and 26. 

Plan multistep syntheses using alcohols as starting materials and intermediates. 

Various sulfuric and phosphoric acid esters have sometimes been used instead of alcohols as starting materials for the preparation of nitriles. Of more general importance are sulfonates, particularly from methane- or p-toluene-sulfonic acid, which react in an 5N2-type substitution with cyanide ions. The most common starting materials are, as described in Section 1.8.1.2.1, alkyl halides, and if their preparation creates problems, the use of sulfonates may be advantageous. The addition of crown ethers or the... 

Most of the C-X disconnections from Chapters 2-9 eventually led back to alcohols as starting materials. This chapter has introduced the building up of... 

We will use a number of naturally derived amino alcohols as starting materials in this chapter. 

Besides the ether sulfates derived from coconut oil fatty alcohols, it is possible to produce other compounds with a higher degree of ethoxylation by using, other alcohols as starting materials. In this way, the hydrophilic/lipophilic balance (HLB) value can be widely varied. Thus, additives can be produced for oil-in-water (OAV) or water-in-oil (W/O) emulsions, for use in saline water, for detergents, and for dispersants of lime soap. 

Masson and coworkers reported a-alkylation of imines through a three-component radical/cation domino process using bromomalonate 11, an enamide 13, and an alcohol as starting materials. First, an iridium species forms the alkyl radical 12 from 11 by single electron transfer (SET). Then enamide 13 reacts with 12 to produce the amidoalkyl radical 14. An oxidative radical-polar crossover reaction then furnishes an N-acyliminium cation 15, which finally reacts with nucleophilic alcohol to produce a-alkylated a-amido ether 16 (Scheme 5.5) [11]. 

Chiou et (d. [81] investigated the hydroformylation-acetalization in the framework of the synthesis of pyrrolidinoindolines and tetrahydrofuranoin-dolines (Scheme 5.89). The hydroformylation occurred in the a-position of the aryl ring. Double cyclization constructed the fused pyrrolidine ring in a stereoselective maimer. Based on this protocol, a variety of pharmacologically important alkaloids were synthesized. By application of the corresponding allyl alcohol as starting material, the THF-based physovenine was prepared. 

The El dehydration of 2° and 3° alcohols is illustrated with (CH3)3COH (a 3° alcohol) as starting material to form (CH3)2C=CH2 as product (Mechanism 9.1). The mechanism consists of three steps. 

Propose efficient syntheses for each of the following ethers, using haloaUcanes or alcohols as starting materials. 

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