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.

Article abstract of DOI:10.1016/0040-4039(88)85135-9

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.