Synthese und Reaktionen Chinuclidin‐stabilisierter Sulfene, R¹R²CSO₂←N(CH₂CH₂)₃CH

Abstract

Synthesis and Reactions of Quinuclidine‐Stabilized Sulfenes, R 1 R 2 CSO 2 ←N(CH 2 CH 2 ) 3 CH Quinuclidine adducts of the sulfenes 3 and 10 have been isolated and have proven to be good sources for investigating the reactivity of the respective sulfenes. Water and some alcohols react with 3 as well as with “disulfene” ( 5 ) in the presence of quinuclidine ( 2 ) under formation of the corresponding (alkyl)chinuclidinium methanesulfonyl methanesulfonates 6a – f . The expected intermediate mesyl methanesulfonic acid esters could only be isolated in the case of 4 . Similar results were obtained on attempted synthesis of methylsulfene. Only the noncyclic dimer 10 could be prepared, which reacts with alcohols or water forming 11a – c . The formation of “monomeric” sulfene or methylsulfene under these conditions could be ruled out by comparison with their expected hydrolysis products 8 and 13 , which were synthesized separately.