Reaction with acyl halides

Reaction with Acyl Halides. Acyl halides react at loom tempeiatuie with mono- and dialkanolamines to give amides (10,11). 

Reaction with acyl halides, esters, or thioesters affords the acylstannanes R SnCOR2, with thioesters giving the cleanest reactions (Equation (44)).84,156... 

Occasionally, N-acylation is the predominant reaction with acyl halides. Thus ethyl chloroformate or diethyl carbonate on reaction with (171c) leads only to the urethane (200) (91T497). 

Reactions with Acyl Halides. The palladium-carbon bond in alkyl VII and acyl VIII complexes also can be broken by acyl and alkyl halides, respectively, to give ketones (55). The reaction of the benzyl complex Vila with acetyl chloride in the presence of 2,6-lutidine provided good yield of methyl benzyl ketone, XVII. In the absence of the base, lower yields (26% ) were obtained. Surprisingly, a similar reaction between the benzyl complex and an excess of phenylacetyl chloride afforded a 156% yield of dibenzyl ketone, XVIII, based on the starting benzyl complex (see bottom of p. 105). 

The relative weakness of the carbon-tin bond provided a useful method for carbon-carbon bond formation by cross-coupling reaction with acyl halides. This reaction has been applied for the two-step synthesis of a-ketocyclopropyl sulfones (equation 8)30. 

H. Cross-coupling Reactions with Acyl Halides. 1291... 

REACTIONS WITH ACYL HALIDES, ANHYDRIDES, ESTERS AND... 

Some reactions with acyl halides with magnesium under Barbier conditions also appear to involve acylmagnesium intermediates [3]. 

Enamines may be regarded as synthetic equivalents of enolate ions and are closely related to the enolates derived from ketones in their reactions with acyl halides, alkyl halides and a,3-unsaturated compounds. 

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