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Oxidative cationic cyclization reactions effected by pyridinium chlorochromate

โœ Scribed by E.J. Corey; Dale L. Boger


Book ID
104245825
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
312 KB
Volume
19
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Pyridinium chlorochromate (PCC), C5H5NkClCr03, first introduced as an oxidizing reagent for alcohols just three years ago, 1 has found widespread use in organic synthesis. 2 In earlier work advantage was taken of the mildly acidic character of the reagent to bring about an essentially one-step conversion n (70% yield) of (-)-citronellol (l_) to (-)-pulegone (s), ' a useful reagent for asymmetric synthesis of prostaglandins. 4 The effectiveness of this synthesis together with our interest in exploring new techniques for


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Kinetics of oxidation of 24 S-Arylmercaptoacetic acids (SAMA) by pyridinium chlorochromate (PCC) have been studied in acidmedium. The product of oxidation is the corresponding thiophenol. The rate data of meta-and para-substituted acids have been correlated well with I , R o values and the meta-comp