EPISULFONIUM SALTS .I. CARBON VS SULFUR ATTACK IN REACTION OF CYCLOOCTENE-S-METHYLEPISULFONIUM ION WITH NUCLEOPHILES

The reaction of cyclooctene-S-methylepisulfonium 2,4,6-trinitrobenzenesuIfonate (1) with a variety of nucleophilic reagents is shown to occur more often by attack at sulfur to give a sulfenyl compound and cyclo-octene than on carbon to give a 1,2-disubstituted cyclooctane. The yields of cyclooctene, formed in the presence of excess cyclohexene, in most cases appear to correlate roughly with the relative “softness” of the attacking nucleophile as defined by the Pearson theory of hard and soft acids and bases. © 1969, American Chemical Society. All rights reserved.