1998
DOI: 10.1055/s-1998-1583
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Chemical Manganese Dioxide (CMD), an Efficient Activated Manganese Dioxide. Application to Oxidation of Benzylic and Allylic Alcohols

Abstract: Oxidation of benzylic and allylic alcohols with chemical manganese dioxide smoothly proceeded under mild reaction conditions to give the corresponding aldehydes and ketones, respectively, in high yields.

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Cited by 72 publications
(30 citation statements)
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“…Using Click chemistry, 5 the triazol rings 6 and 7 were obtained in 83% and 38% yield, respectively. The allylic alcohol in 7 was oxidized with manganese dioxide 6 to give the corresponding ketone 8 (92%). .…”
Section: Resultsmentioning
confidence: 99%
“…Using Click chemistry, 5 the triazol rings 6 and 7 were obtained in 83% and 38% yield, respectively. The allylic alcohol in 7 was oxidized with manganese dioxide 6 to give the corresponding ketone 8 (92%). .…”
Section: Resultsmentioning
confidence: 99%
“…Usually, a large excess of CMD was required for smooth completion of the reactions. In some cases, Wako CMD proved to be much superior to the usual AMDs commercially available from the Aldrich, Fluka, Merck, Nakarei and Wako companies [6]. These papers prompted us to repeat our earlier iodination experiments [1], but using the said two CMD brands as the oxidants (see Experimental).…”
Section: Introductionmentioning
confidence: 95%
“…In 1998, four Japanese papers were published [6][7][8][9] in which selective oxidations of various classes of organic compounds were reported, using Wako CMD as the effective oxidant. These heterogeneous reactions, carried out in hexane, CH 2 Cl 2 or acetone, often proceeded in nearly quantitative yields under relatively mild conditions.…”
Section: Introductionmentioning
confidence: 99%
“…Thus, substrates 4 were obtained by the addition of the enolate of ethyl acetate to either an aldehyde or an acyl chloride. In the case of the addition to the aldehyde, [13] the resulting alcohol was oxidized with MnO 2 [14] or DMP (Dess-Martin periodane). [15] Subsequent Knoevenagel condensation of the β-keto ester 3 with the appropriate aldehyde gave the desired dialkenyl ketones [16] with overall yields of 29-71 % (Table 1).…”
Section: Introductionmentioning
confidence: 99%