The Manganese Dioxide Oxidation of Allylic Alcohols

1959 ◽  
Vol 24 (8) ◽  
pp. 1051-1056 ◽  
Author(s):  
ROY J. GRITTER ◽  
THOMAS J. WALLACE
Keyword(s):  
Manganese Dioxide ◽  
Allylic Alcohols

scholarly journals Efficient Solvent-free Oxidation of Benzylic and Aromatic Allylic Alcohols and Biaryl Acyloins by Manganese Dioxide and Barium Manganate

1999 ◽  
Vol 23 (3) ◽  
pp. 236-237
Author(s):  
Habib Firouzabadi ◽  
Babak Karimi ◽  
Mohammad Abbassi
Keyword(s):  
Manganese Dioxide ◽  
Solvent Free ◽  
Allylic Alcohols ◽  
Solvent Free Conditions ◽  
Free Oxidation

Active manganese dioxide and commercially available barium manganate are used for the efficient oxidation of benzylic and aromatic allylic alcohols and biaryl acyloins under solvent-free conditions.

ChemInform Abstract: Oxidation by Chemical Manganese Dioxide. Part 3. Oxidation of Benzylic and Allylic Alcohols, Hydroxyarenes and Aminoarenes.

ChemInform ◽  
2010 ◽  
Vol 30 (20) ◽  
pp. no-no
Author(s):  
Masao Hirano ◽  
Sigetaka Yakabe ◽  
Hideki Chikamori ◽  
James H. Clark ◽  
Takashi Morimoto
Keyword(s):  
Manganese Dioxide ◽  
Allylic Alcohols ◽  
Chemical Manganese Dioxide

Chemical Manganese Dioxide (CMD), an Efficient Activated Manganese Dioxide. Application to Oxidation of Benzylic and Allylic Alcohols

Synlett ◽  
1998 ◽  
Vol 1998 (01) ◽  
pp. 35-36 ◽  
Author(s):  
Toyohiko Aoyama ◽  
Naoko Sonoda ◽  
Mariko Yamauchi ◽  
Kyoko Toriyama ◽  
Masahiro Anzai ◽  
...  
Keyword(s):  
Manganese Dioxide ◽  
Allylic Alcohols ◽  
Chemical Manganese Dioxide

Oxidation by Chemical Manganese Dioxide. Part 3.1 Oxidation of Benzylic and Allylic Alcohols, Hydroxyarenes and Aminoarenes

1998 ◽  
pp. 770-771 ◽  
Author(s):  
Masao Hirano ◽  
Sigetaka Yakabe ◽  
Hideki Chikamori ◽  
James H. Clark ◽  
Takashi Morimoto
Keyword(s):  
Manganese Dioxide ◽  
Allylic Alcohols ◽  
Chemical Manganese Dioxide

ChemInform Abstract: Chemical Manganese Dioxide (CMD), an Efficient Activated Manganese Dioxide. Application to Oxidation of Benzylic and Allylic Alcohols.

ChemInform ◽  
2010 ◽  
Vol 29 (17) ◽  
pp. no-no
Author(s):  
T. AOYAMA ◽  
N. SONODA ◽  
M. YAMAUCHI ◽  
K. TORIYAMA ◽  
M. ANZAI ◽  
...  
Keyword(s):  
Manganese Dioxide ◽  
Allylic Alcohols ◽  
Chemical Manganese Dioxide

An Apparent Stereochemical Effect in MnO2 Oxidation of Some Allylic Alcohols

1971 ◽  
Vol 49 (18) ◽  
pp. 3038-3045 ◽  
Author(s):  
Bert Fraser-Reid ◽  
Bernard J. Carthy ◽  
N. L. Holder ◽  
Mark Yunker
Keyword(s):  
Hydrogen Bonding ◽  
Manganese Dioxide ◽  
Hydroxyl Group ◽  
Allylic Alcohols ◽  
Unsaturated Ketone ◽  
Anomeric Effect ◽  
Chair Form ◽  
Large Separation ◽  
Acid Catalyzed

3,4-Di-O-acetyl-D-xylal undergoes acid-catalyzed reaction with ethanol to give the anomeric mixture of ethyl 2,3-dideoxy-4-O-acetyl-D-glycero-pent-2-enopyranosides which can be separated after deacetylation. The α-D anomer 1 is readily oxidized by manganese dioxide to the α,β-unsaturated ketone but the β-D anomer 2 is inert. Thorough investigation of the 100 and 220 MHz n.m.r. spectra of 1 and 2, their acetates, and dinitrobenzoates indicates that each exists conformationally pure in the half-chair form having the benefit of the anomeric effect. Hence in the oxidizable anomer 1 the C-4 allylic hydroxyl group is pseudo-equatorial; in the unoxidizable one it is pseudoaxial. Hydrogen bonding does not appear to be the reason for failure of 2 to oxidize.The ethoxy groups of 1 and 2 are found to be ABX3 system with unusually large separation for the AB protons.

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