4883-01-6Relevant academic research and scientific papers
DEPROTECTION OF CARBONYL GROUPS BY ANODIC OXIDATION OF DITHIOACETALS: A KEY STEP IN THE SYNTHESIS OF α-DIONES, α-KETOLS AND CHIRAL SYNTHONS.
Martre, Anne-Marie,Mousset, Guy,Rhlid, Rachid Bel,Veschambre, Henri
, p. 2599 - 2602 (1990)
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.
2-Benzoyl-2-methyl-1,3-dithiane
Stahl, Ingfried,Schomberg, Iris,Frenzen, Gerlinde
, p. 2179 - 2182 (1999)
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
Anomalous C-C bond cleavage in sulfur-centered cation radicals containing a vicinal hydroxy group
Li, Zaiguo,Kutateladze, Andrei G.
, p. 8236 - 8239 (2007/10/03)
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.
Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
, p. 2125 - 2154 (2007/10/03)
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
Direct Ni° mediated synthesis of ketones from acyl bromides and Grignard reagents
Malanga, Corrado,Aronica, Laura A.,Lardicci, Luciano
, p. 9185 - 9188 (2007/10/02)
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.
REACTIONS OF METALLATED 1,3-DITHIANES WITH CARBOXYLIC ACID DERIVATIVES
Page, Philip C. Bulman,van Niel, Monique B.,Westwood, Donald
, p. 269 - 276 (2007/10/02)
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
Chemistry of Aminoketene Dithioacetals: Preparation of Protected α-Amino Aldehydes and Ketones and Formation of Nitrogen Heterocycles
Page, Philip C. Bulman,Niel, Monique B. van,Westwood, Donald
, p. 775 - 776 (2007/10/02)
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
Reaction of 1,3-Dithiane with Nitriles: Generation of Primary Aminoketene Thioacetals
Page, Philip C. Bulman,Niel, Monique B. van,Williams, P. Howard
, p. 742 - 743 (2007/10/02)
The anions derived from 1,3-dithiane and 2-trimethylsilyl-1,3-dithiane react with simple nitriles to provide primary aminoketene thioacetals.
