Aromatics with Halogenated Side Chain

AROMATIC NITRO COMPOUNDS WITH OTHER FUNCTIONAL GROUPS 

Aromatic Nitro Compounds with Other Functional Groups 

T0138 Calgon Carbon Corporation, Perox-Pure T0236 Electrokinetic Remediation—General 

T0755 Supercritical Carbon Dioxide Extraction—General 

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Aromatics with Halogenated Side Chain Aromatics with Halogenated Side Chain Benzyl Chloride Chlorotoluene, Alpha DDT Trichloro(chlorophenyl,4-bis) Ethane Arsenic... 

Benzyl chloride Chlorotoluene, alpha under Aromatics with Halogenated Side Chain Beryllium... 

DDD Dichloro(chlorophenyl)-bis Ethane under Ring-Substituted Aromatics DDE Dichlorodiphenyldichloroethylene under Ring-Substituted Aromatics DDT Trichloro(chlorophenyl-l,4- bis) Ethane under Aromatics with Halogenated Side Chain Decane, n under Alkanes and Cyclic Alkanes... 

Nature utilizes the shikimate pathway for the biosynthesis of amino acids with aryl side chains. These nonprotein amino acids are often synthesized through intermediates found in the shikimate pathway. In many cases, L-a-amino acids are functionalized at different sites to yield nonprotein amino acids. These modifications include oxidation, hydroxylation, halogenation, methylation, and thiolation. In addition to these modifications, nature also utilizes modified biosynthetic pathways to produce compounds that are structurally more complex. When analyzing the structures of these nonprotein amino acids, one can generally identify the structural similarities to one of the L-a-amino acids with aromatic side chains. 

Aliphatic mono-halides, and aromatic hydrocarbons with halogen in side-chain, precipitate silver hdide on treatment with cold aqueous silver nitrate solution. 

Oxidation of side chains. The oxidation of halogenated toluenes and similar compounds and of compounds with side chains of the type —CHjCl and —CH OH proceeds comparatively smoothly with alkaline permanganate solution (for experimental details, see under AromcUic Hydrocarbons, Section IV.9,6 or under Aromatic Ethers, Section IV,106). The resulting acid may be identified by a m.p. determination and by other teats (see Section IV,175). 

This enzyme [EC 1.1.1.96] catalyzes the reversible reaction of )3-(3,5-diiodo-4-hydroxyphenyl)lactate with NAD+ to produce )3-(3,5-diiodo-4-hydroxyphenyl)pyru-vate and NADH. The substrates for this enzyme must contain an aromatic ring with a pyruvate side chain (or lactate), the most active substrates being halogenated derivatives. Potential substrates with hydroxyl or amino groups in the 3 or 5 position are inactive. 

Side-Chain Chlorination of Arylalkanes. Alkyl-substituted aromatic compounds can easily be halogenated at the benzylic position with chlorine or bromine.107 108,142 143 a-Monohaloalkylaromatics are usually the main products with both reagents. 

Fittig applied the reaction to aromatic hydrocarbons. In this latter case a second side-chain may be introduced from a di-halogen derivative, simultaneously with the first or subsequently in a second reaction. All the possibilities of the reaction are illustrated in the synthesis of anthra-... 

Alkyl chlorides and bromides, aromatic compounds containing halogen in the side chain, or nuclear-halogenated aromatic compounds with nitro groups in the ortho and/or para position, do not usually react readily at room temperature but react fairly rapidly on heating. The order of reactivity of alkyl halides is tertiary > secondary > primary, and indeed some tertiary halides may react in the cold. 

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