Abstract
Synthesis and Reactions of Quinuclidine‐Stabilized Sulfenes, R1R2CSO2←N(CH2CH2)3CHQuinuclidine 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.
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