89959-83-1Relevant academic research and scientific papers
The chemistry of α,β-ditosyloxyketones: Novel routes for the synthesis of desoxybenzoins and α-aryl-β-ketoaldehyde dimethylacetals from α,β-chalcone ditosylates
Prakash, Om,Kumar, Rajesh,Sharma, Deepak,Pannu, Kamaljeet,Kamal, Raj
, p. 2189 - 2192 (2007)
The reaction of α,β-chalcone ditosylates 3 with potassium hydroxide in suitable conditions leads to 1,2-aryl shift and carbon-carbon bond cleavage, thereby providing a novel route for the synthesis of 1,2-diarylethan-1-ones 4 and 1,2-diaryl-3,3-dimethoxy propan-1-ones 5. Georg Thieme Verlag Stuttgart.
The chemistry of α,β-ditosyloxy ketones: A new and convenient route to 4,5-diarylisoxazoles from α,β-chalcone ditosylates
Kamal, Raj,Sharma, Deepak,Wadhwa, Deepak,Prakash, Om
scheme or table, p. 93 - 96 (2012/02/03)
The reaction of α,β-chalcone ditosylates with hydroxyl-amine hydrochloride under suitable conditions leads to a 1,2-aryl shift, thereby providing a new route to 4,5-disubstituted isoxazoles. Georg Thieme Verlag Stuttgart. New York.
The chemistry of α,β-ditosyloxyketones: new and convenient route for the synthesis of 1,4,5-trisubstituted pyrazoles from α,β-chalcone ditosylates
Prakash, Om,Sharma, Deepak,Kamal, Raj,Kumar, Rajesh,Nair, Reshmi R.
experimental part, p. 10175 - 10181 (2010/02/27)
The reaction of α,β-chalcone ditosylates with various reagents such as phenylhydrazine hydrochloride, semicarbazide hydrochloride and thiosemicarbazide in suitable conditions leads to 1,2-aryl shift, thereby providing a novel route for the synthesis of 1,4,5-trisubstituted pyrazoles.
Reaction Manifolds of Alkenes with benzene: Stereospecific syn-1,2-Ditosyloxylation of the Carbon-Carbon Double Bond and Other Processes
Rebrovic, Louis,Koser, Gerald F.
, p. 2462 - 2472 (2007/10/02)
The treatment of various alkenes with benzene (1) in CH2Cl2 gives moderate yields of the corresponding vic-bis(tosyloxy)alkanes (2).When cis- and trans-2-butenes, cis- and trans-2-pentenes, cis-3-hexene, cis-4-octene, and cyclohexene are reactants, the tosyloxy ligands are introduced with syn stereospecifity.With cis- and trans-stilbenes, however, a mixture of meso- and dl-1,2-diphenyl-1,2-bis(tosyloxy)ethanes results from either alkene.Some alkenes react with 1 in a different way.Thus, trans-3-hexene and trans-4-octene with 1 give low yields of 2,5-bis(tosyloxy)-3-hexene and 3,6-bis(tosyloxy)-4-octene, respectively.Evidence is presented that the formation of the bis(tosyloxy)alkenes proceeds via initial oxidation of the trans alkenes by 1 to conjugated dienes and subsequent conjugate ditosyloxylation of the dienes.In a few cases, molecular rearrangements occur.Thus, norbornene with 1 gives 2,7-bis(tosyloxy)norbornane, among other products, while 1,1-diphenylethylene gives deoxybenzoin (major product) and (β,β-diphenylethenyl)phenyliodonium tosylate.The reaction of styrene with 1 depends on the medium; when CH2Cl2 is present, the product is 1-phenyl-1,2-bis(tosyloxy)ethane, but in the absence of solvent, the product is 1,1-bis(tosyloxy)-2-phenylethane.Most alkenes react with 1 to give p-toluenesulfonic acid as a byproduct, and, in rare instances, (iodoxy)benzene is obtained.A mechanism for the vic-ditosyloxylation of alkenes by 1, consistent with the observed syn stereospecificity, is proposed.
