- DEPROTECTION OF CARBONYL GROUPS BY ANODIC OXIDATION OF DITHIOACETALS: A KEY STEP IN THE SYNTHESIS OF α-DIONES, α-KETOLS AND CHIRAL SYNTHONS.
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The anodic oxidation of α-keto and α-hydroxythioacetals provides an efficient way for the regeneration of α-diones and α-ketols, specially in the cases where chemical reactions are unsuccessful.
- Martre, Anne-Marie,Mousset, Guy,Rhlid, Rachid Bel,Veschambre, Henri
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- 2-Benzoyl-2-methyl-1,3-dithiane
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The crystal structure of the title compound, C12H14OS2, shows a 1,3-dithiane ring adopting a chair conformation with the 2-benzoyl group orientated axially. The carbonyl-O atom lies above the heterocycle, but is asymmetric
- Stahl, Ingfried,Schomberg, Iris,Frenzen, Gerlinde
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- Anomalous C-C bond cleavage in sulfur-centered cation radicals containing a vicinal hydroxy group
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1,3-Dithianyl cation radicals having α-hydroxy-neopentyl or similar groups in position 2, which are generated via oxidative photoinduced electron transfer, undergo anomalous fragmentation necessitating refinement of the accepted mechanism. Experimental and computational data support a rationale in which proton abstraction from the hydroxy group in the initial cation radical does not cause a Grob-like fragmentation, but rather produces a neutral radical species, the alkoxy radical, that undergoes fragmentation in either direction, i.e., cleaving the C-C bond to dithiane or to the tertiary alkyl group.
- Li, Zaiguo,Kutateladze, Andrei G.
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p. 8236 - 8239
(2007/10/03)
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- Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
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Enantioselective sulphoxidation of a wide range of 2-substituted-1,3-diathianes has been carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide deriva
- Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
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p. 2125 - 2154
(2007/10/03)
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- Direct Ni° mediated synthesis of ketones from acyl bromides and Grignard reagents
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A catalytic amount of NidppeCl2 converts an acyl bromide directly into ketones at 0°C in THF in the presence of a Grignard reagent. The described procedure represents a useful way to afford dialkyl, diaryl or alkyl aryl ketones as well as 1,2-diketones. In the adopted reaction conditions double bonds, esters and ketones are unaffected.
- Malanga, Corrado,Aronica, Laura A.,Lardicci, Luciano
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p. 9185 - 9188
(2007/10/02)
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- REACTIONS OF METALLATED 1,3-DITHIANES WITH CARBOXYLIC ACID DERIVATIVES
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2-Lithio-1,3-dithiane and 2-lithio-2-trimethylsilyl-1,3-dithiane react with nitriles to afford primary aminoketene dithioacetals in good yields; these compounds exhibit marked ambident nucleophilicity.Use of other carboxylic acid derivatives as electrophi
- Page, Philip C. Bulman,van Niel, Monique B.,Westwood, Donald
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p. 269 - 276
(2007/10/02)
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- Chemistry of Aminoketene Dithioacetals: Preparation of Protected α-Amino Aldehydes and Ketones and Formation of Nitrogen Heterocycles
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The ambient anion (2) derived from primary aminoketene dithioacetal (1, R = Ph) reacts with alkyl halides at the carbon atom to give remarkably stable imines which may be reduced to give protected α-amino ketones using borane in quantitative yield, and un
- Page, Philip C. Bulman,Niel, Monique B. van,Westwood, Donald
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p. 775 - 776
(2007/10/02)
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- Reaction of 1,3-Dithiane with Nitriles: Generation of Primary Aminoketene Thioacetals
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The anions derived from 1,3-dithiane and 2-trimethylsilyl-1,3-dithiane react with simple nitriles to provide primary aminoketene thioacetals.
- Page, Philip C. Bulman,Niel, Monique B. van,Williams, P. Howard
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p. 742 - 743
(2007/10/02)
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