Halides functional group interconversion

Figure 6.13 Functional group interconversions of methyl, primary, and secondary alkyl halides using Sn2 reactions.

Furazan- and furoxan-carboxylic acids are thermally and hydrolytically unstable decomposing to a-(hydroxyimino)nitriles, but their amide, ester, halide, and nitrile derivatives are readily accessible and all undergo the expected functional group interconversions. Dicyanofuroxan reacts with hydroxylamine to give the fused oxazino compound (63) and the pyridazino analogue (64) is similarly formed with hydrazine <82H(19)1063>. 

Some synthetic uses of halides II. FUNCTIONAL GROUP INTERCONVERSION OF HALIDES... 

The replacement of halogen atoms in halides by alkoxide or thiolate ions is normally viewed as an alkylation of the olate moiety. For the purposes of this review we will consider this synthetically useful functional group interconversion as a nucleophilic displacement reaction of the halide by which ether and sulfide moieties are introduced into organic compounds. 

One of the key functional group interconversions of halides is that they may be readily oxidized into aldehydes and ketones. Using the methodology described below, many... 

Sn2 reactions are highly useful in organic synthesis because they enable us to convert one functional group into another—a process that is called a funcdonal group trausfonna-tion or a functional group interconversion. With the Sn2 reactions shown in Fig. 6.11, methyl, primary, or secondary alkyl halides can be transformed into alcohols, ethers, thiols, thioethers, nitriles, esters, and so on. Note. The use of the prefix thio- in a name means that a sulfur atom has replaced an oxygen atom in the compound.)... 

B. Functional Groups — Preparation, reactions, and interconversions of alkanes, alkenes, alkynes, dienes, alkyl halides, alcohols, ethers, epoxides, sulfides, thiols, aromatic compounds, aldehydes, ketones, carboxylic acids and their derivatives, amines... 

A diagram showing six different functional groups and their relative oxidation states. The interconversion between alkenes, alcohols, and alkyl halides does not constitute oxidation or reduction. 

FUNCTIONAL GROUP D. Hydrolysis of Alkyl Halides INTERCONVERSION BY NUCLFOPHILIC ... 

When complex organic systems have evolved in nature, they are frequently made by the combination of carboxy carbonyl groups and the heteroatoms of alcohols, amines, or thiols. Why The addition-elimination processes introduced in Chapter 19 provide mechanistic pathways of relatively low activation energy for the interconversion of variously substituted carboxylic acid derivatives, many of which play central roles in biology (Chapter 26). Chemists find these compounds similarly useful, as we shall see in this chapter, which deals with the chemistry of four major carboxylic acid derivatives halides, anhydrides, esters, and amides. Each has a substituent, L, that can function as a leaving group in substitution reactions. We already know, for instance, that displace-O... 

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