By Riedel, E.
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Speedily expanding curiosity within the difficulties of pollution and source-receptor relationships has ended in an important growth of information within the box of atmospheric chemistry. often the chemistry of atmospheric hint ingredients is ruled via the oxygen content material of the ambience. Upon coming into the ambience in a roughly decreased nation, hint ingredients are oxidized through a number of pathways and the generated items are usually precursors of acidic compounds.
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Two patterns of reaction mechanism have been proposed for the oxidation of alcohols under neutral conditions. The first mechanism involves Table 1. 46 ' ( Iz VS. 15M (C,HgI,NBF, bThese values are almost the same as E'/2 vs. 01 M Ag+ 29 2. Anodic Oxidations removal of one electron from the lone-pair electrons of the oxygen atom as the initiation step (1 )-1), while the initiation process in the second mechanism involved abstraction of a hydrogen atom from the position II to oxygen (1 )-2). Under strongly basic conditions, the oxidation of the alkoxide anion is the initiation step (l )-3).
CSHs )2 S- 0R - CI- (CSHS)2S0 + RCl Y=9S% (R=C8H17) Y=90% (R=CSHSCH2CH2CH2) (11) The SN2-like character of the reaction of chloride anion with sulfonium salts has been clearly demonstrated by the almost complete inversion of configuration observed in the transformation of S-( + )-2-octanol to R -( - )-2chlorooctane (12). 5 % ) (12) Y=7S% (R(-). S%) 41 2. Anodic Oxidations Some 1,4- and I,5-diols are converted into the corresponding cyclic ethers under the same reaction conditions (13). 3. Anodic cleavage of a carbon-sulfur bond has been observed in the oxidation of bis(phenylthio)methane in acetonitrile at a platinum electrode using sodium or tetraethylammonium perchlorate as the supporting electrolyte.
R-CHOH ~ R-CHO -H+ (4) R-C02H Some typical results are listed in Table 2. Table 2. Oxidation of Primary Alcohols to Carboxylic Acids on a Nickel Hydroxide Anode R in RCH20H Reaction system Yield ("10) R in RCH20H Reaction system Yield ("10) C3 H7 B 92 CsH" B 91 CH30-o-CH2 B 90· CsHu A 84 Cl-o-CH2 B 71· C7 H,S A 89 70· A 89 o- B Ca H'7 C9H'9 A 87 CH30-Q- B 83 b C"H23 A 80 HO-o- B 67 b C'7 H3S A 77 79 73 G.. 0 A A A 76 ~CH A 10 CH::C A 51 /\d B 34 0- A 86 ~CH2 A 82 02 N- Q - B 91· ~CH2A 68 ·See ref.