124745-26-2Relevant academic research and scientific papers
Subsituted 4-(2-alkenylsulfinyl)morpholines : preparation and conversion into the corresponding sulfinic acids and esters. Stereochemistry of olefin formation by hydrolytic desulfinylation of allylic sulfinamides.
Baudin, Jean-Bernard,Julia, Sylvestre
, p. 196 - 214 (2007/10/02)
By reaction with 4-(chlorosulfenyl)morpholine in the presence of triethylamine, several substituted allylic alcohols have been converted into the title sulfinamides.As a complementary method, the new α-lithio allylic sulfinamides have been prepared and efficiently alkylated with organic halides.The boron trifluoride-etherate catalyzed treatment of the allylic sulfinamides with simple saturated alcohols provided the corresponding alkyl sulfinates while propargylic and allylic alcohols opened a route to various α,α'-bis-unsaturated sulfones.Efficient conditions for the acid-catalyzed hydrolysis of allylic sulfinamides are described and some allylic sulfinic acids bearing an electron-withdrawing group were isolated.Smooth fragmentation of the homoconjugated sulfinic acids gave the corresponding (E)-olefins stereoselectively. - Key words: sigmatropic rearrangement / allylic sulfinamide / allylic sulfinic ester / organolithium derivative / sulfone / retro-ene reaction / sulfur dioxide elimination / stereochemistry
Diastereoselectivity in the [2,3]-sigmatropic rearrangement of substituted allylic N,N-dialkylamidosulfoxylates. X-ray molecular structure of [(1′) S*, (S)S*]-(2′E)-4-[[3′-(4″-bromophenyl)-1′-methyl- 2′-propenyl]sulfinyl]-morpholine
Baudin, Jean-Bernard,Bkouche-Waksman, Itka,Hareau, Georges,Julia, Sylvestre A.,Lorne, Robert,Pascard, Claudine
, p. 6655 - 6672 (2007/10/02)
By the reaction with three N,N-dialkylamidosulfenyl chlorides 2 bearing representative sizes for the R groups on the nitrogen atom, several substituted secondary E or Z allylic alcohols (1a-h) have been converted into the corresponding pairs of diastereoisomeric allylic sulfinamides (3+-3′a-v), whose ratios have been determined by 1H NMR spectroscopy. Five cases of entirely diastereoselective [2,3]-sigmatropic rearrangement have been observed. The stereochemistry of one pure diastereoisomer 3′m has been determined by single crystal X-Ray analysis. When treated with 4-morpholinesulfenyl chloride, cyclohex-2-en-1-ol is stereoselectively converted to one diastereoisomer of the sulfinamide 5b which, by unambiguous procedures, led to the sane p.tolylsulfoxide 5a already obtained by treatment of cyclohex-2-en-1-ol with toluene-p-sulfenyl chloride.
THE LITHIATION AND ALKYLATION OF 4-(2'-ALKENESULPHINYL)-MORPHOLINES, A SIMPLE ROUTE TO SUBSTITUTED ALLYLIC SULPHINAMIDES
Baudin, Jean-Bernard,Julia, Sylvestre A.
, p. 1963 - 1966 (2007/10/02)
By the reaction with 4-morpholinesulphenyl chloride carried out in the presence of trimethylamine, several substituted allylic alcohols have been converted into the corresponding allylic sulphinamides 2.As a complementary method, the new lithio-derivative
