110210-98-5Relevant academic research and scientific papers
New Routes to Heterocycles via Sulphenylation of Unsaturated Amides
Samii, Zakaria K. M. Abd El,Ashmawy, Mohamed I. Al,Mellor, John M.
, p. 2517 - 2522 (2007/10/02)
The reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of N-allylacetamide, followed by hydrolysis, affords a vicinal hydroxy sulphide.Similarly, addition to N-allyltrifluoroacetamide affords hydroxy sulphide adducts, but with different regioselectivity.N-Allylbenzamide and other unsaturated benzamides under similar conditions give cyclic products, 4,5-dihydro-1,3-oxazoles.Homoallylic amides give 5,6-dihydro-4H-1,3-oxazines.Amides derived from pent-4-enylamine give substituted pyrrolidines by cyclisation through nitrogen, but N-hex-5-enylbenzamide gives only an acyclic adduct.Unsaturated carboxylic acids and unsaturated carboxamides are transformed in good yield into lactones under similar conditions.
REGIOSELECIVE HYDROXYSULPHENYLATION OF DERIVATIVES OF ALLYLIC ALCOHOLS AND AMINES
Samii, Zakaria K M Abd El,Ashmawy, Mohamed I Al,Mellor, John M
, p. 5289 - 5292 (2007/10/02)
Reaction of manganic acetate with diphenyldisulphide in dichloromethane-trifluoroacetic acid in the presence of allylic esters or amides of allylamine gives trifluoroacetoxysulphides and hence by ready hydrolysis vicinal hydroxysulphides.The regiochemical outcome can be controlled by selection of either an acetyl- or trifluoroacetyl derivative.
