EVIDENCE FOR A TRIGONAL BIPYRAMIDAL INTERMEDIATE DURING NUCLEOPHILIC-SUBSTITUTION AT A SULFONYL CENTER AND FOR A SULFONYLIUM CATION IN THE ACID-CATALYZED REACTION
Nj. Baxter et al., EVIDENCE FOR A TRIGONAL BIPYRAMIDAL INTERMEDIATE DURING NUCLEOPHILIC-SUBSTITUTION AT A SULFONYL CENTER AND FOR A SULFONYLIUM CATION IN THE ACID-CATALYZED REACTION, Chemical communications, (21), 1997, pp. 2037-2038
The rate of alkaline hydrolysis of a substituted beta-sultam shows a d
ominant term second-order in hydroxide ion, clearly indicating the rev
ersible formation of a monoanionic trigonal bipyramidal intermediate;
substituent effects and kinetic parameters for the acid catalysed hydr
olysis are indicative of the formation of a sulfonylium ion intermedia
te.