Formation from carboxyl

Acid chloride—con l d esters from, 802-803 from carboxylic acids, 794-795 Grignard reaction of, 804-805 hydrolysis of, 802 IR spectroscopy of, 822-823 ketones from, 805 mechanism of formation from carboxylic acids, 795 naming, 786... 

For a general discussion of ketone formation from carboxylic acids and organolithmm reagents, see M. J. Jorgenson, Org React, 18, 1 (1970). 

BORIC ACID CATALYZED AMIDE FORMATION FROM CARBOXYLIC ACIDS AND AMINES N-BENZYL-4-PHENYLBUTYRAMIDE... 

Amide Bond Formation from Carboxylic Acids and Amines... 

For a review of amide formation from carboxylic acids, see Beckwith, in Zabicky, Ref. 555. pp, 105-109. " See, for example, Bladd-Font Tetrahedron Lett. 1988, 21, 2443. 

Acyl cations are now well-established chemical species. They can be prepared in quantity in solution, and several have been isolated as their crystalline salts. Recent papers have described their formation from carboxylic acids and esters under strongly acidic conditions81214, but they are most conveniently available from the reactions of acyl halides with L.ewis acids21 well-defined Lewis acid-base complexes are formed, which decompose in a second stage to the acyl cations21-23, viz. 

NH3 or RNH2 or R2NH Amide formation from carboxylic acid derivatives (mild) or from carboxylic acids (A technical synthesis of nylon-6,6) transamidation [capro-lactame —> nylon-6 (perlon)] Peptide synthesis (Section 6.4.3)... 

Amide formation from carboxylic acids 480 with O-subsituted hydroxylamine hydrochlorides also proceeds in the presence of DCC to give the substituted hydroxamic acid 481 in 91 % yield.451... 

Garcia, J, Uipi, F, Vilarrasa, J, New synthetic tricks. Triphenylphosphine-mediated amide formation from carboxylic acids and azides, Tetrahedron Lett., 25, 4841-4844, 1984. 

Direct ester formation from carboxylic acids (R C02H) and alcohols (R OH) works in acid solution but not in basic solution. Why not By contrast, ester formation from alcohols (R OH) and acid anhydrides [(R CO)20)] or chlorides (R COCI) is commonly carried out in basic solution in the presence of bases such as pyridine. Why does this work ... 

Acid chloride formation from carboxylic acid, see under Carboxylic acid Addition, amine to acrylonitrile, 98, 118 bromine to methyl acrylate, 202 bromine to vinyl acetate, 102 chlorine to methyl acrylate, 202 chlorine to vinyl acetate, 147 HC1 to styrene, 77 HC1 and HBr to acrylonitrile, 82. ... 

This method results in regioselective carboxymethylation of the amino group, so the product of reaction is a well-defined derivative. Several N-carboxyalkylated chitosans were prepared via Schiff base formation from carboxylic acids having aldehyde or keto groups [47-48]. The resulting... 

Sn2 nucleophilic substitutions take place in scC02. The presence of silica-supported onium salts 42 as a phase-transfer catalyst enhances the reaction (Scheme 72). Esters formation from carboxylic acids and alcohols via dehydration also proceeds in scC02. The conversion increases as the CO2 pressure increases. A single homogeneous phase is obtained around the critical point, at which the conversion is maximized. 

Carbonyl addition-elimination n. The single most important type of reaction mechanism which has been applied to the preparation of step-growth polymers is the addition-elimination reaction of the carbonyl double bond of carboxylic acids and carboxylic acid derivatives included in this general type of reaction are esterification amidation and anhydride formation from carboxylic acids, esters, amides, anhydrides and acid halides. 

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