Solvolysis of secondary alkyl tosylates with β-dimethyl and β-nitro, sulphinyl, sulphonyl, or phosphonoyl substituents: fragmentation vs. rearrangement
Abstract
The title compounds either fragment or rearrange on solvolysis in carboxylic acids. The named functional group is either lost as an electrophilic fragment (nitro, phosphonoyl) or migrates to the secondary carbon atom (phenylsulphinyl, phenylsulphonyl, and in one case carbonyl). These results are compared with those for other electronegative groups where 1,4-participation becomes a third possibility.