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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.

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