119099-92-2

Upstream product

• 67-56-1 methanol 
• 119099-69-3 4-<(2-methyl-4-(phenylmethoxy)but-2-enyl)sulfinyl>morpholine 
• 119099-69-3 4-((E)-4-Benzyloxy-2-methyl-but-2-ene-1-sulfinyl)-morpholine 

Relevant 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.

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

UNSATURATED SULFINAMIDES III. CONVERSION OF SEVERAL 4-(2'-ALKENESULFINYL)-MORPHOLINES INTO THE CORRESPONDING SULFINATE ESTERS, UNSYMMETRICAL BISALLYLIC SULFONES AND OLEFINS. ISOLATION OF SOME FUNCTIONALISED 2-ALKENESULFINIC ACIDS.

The boron trifluoride etherate-catalysed treatment of the unsaturated sulfinamides (1a-e) with simple saturated alcohols afforded the corresponding alkyl sulfinates 2 whereas allylic alcohols provided the bisallylic sulfones 4.Efficient conditions for the acid-catalysed hydrolysis of the unsaturated sulfinamides 1 are described and some allylic sulfinic acids bearing an electronwithdrawing group 6 were isolated.Smooth fragmentation of the homoconjugated sulfinic acids gave the corresponding olefins 5 and 7.