Electrooxidative pinacol-type rearrangement of β-hydroxy sulfides. Efficient C-S cleavage mediated by chloride ion oxidation

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4303-4310

  Kimura, Makoto ^a   Kobayashi, Kazutaka ^a   Yamamoto, Yasushi ^a   Sawaki, Yasuhiko ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE; KETONE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029865106     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00130-5     Document Type: Article

References (37)

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26. This electrooxidative rearrangement is possible for β-hydroxysulfides other than benzylic sulfides 1. For example, electrolysis of 2-methyl-1-phenyl-2-phenylthio-1-propanol with 6 F/mol of electricity in MeCN-4% MeOH containing tetraethylammonium chloride gave a rearrangement product 2-methyl-2-phenylpropanol in 18% isolated yield. Similarly, 1-[methoxy(phenylthio)methyl]cyclopentanol underwent a low yield (ca. 10%) of rearrangement giving 2-methoxycyclohexanone. Therefore, utilization of benzylic sulfides 1 in the present rearrangement seems to be more appropriate to effect an efficient C-S cleavage and stabilization of the resulting cationic species (see Scheme I).
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