2-TOSYLOXYMETHYLCYCLANONES: RING SIZE DEPENDENCE OF FRAGMENTATION VERSUS INTRAMOLECULAR ALKYLATION

Article abstract of DOI:10.1016/S0040-4020(01)86758-2

The results reported seem to indicate, that in the presence of a nucleophilic base intramolecular alkylation is the normal reaction mode of tosyloxymethylcyclanones of type 14 and that the fragmentation reaction of five-membered compounds is the exception, probably because of the high steric energy of the alkylation transition states, e.g. of type E.