Azulenesulfonium and azulenebis(sulfonium) salts: Formation by interrupted Pummerer reaction and subsequent derivatisation by nucleophiles
Carlos M. López-Alled, Frederick J.O. Martin, Kuan‐Yu Chen, Gabriele Kociok‐Köhn, Tony D. James, Jannis Wenk, Simon E. Lewis
Abstract
Azulenes undergo either single or dual SEAr reactions depending on the nature of the sulfur(IV) electrophile employed. These electrophiles are generated in situ from either sulfoxides or sulfides. The resultant cationic or dicationic azulene products can undergo further derivatisation by means of nucleophilic attack at the sulfonium α-carbon. In the case of cycloalkyl azulenylsulfonium salts, this leads to ring-opened azulenylsulfide products.
Topics & Concepts
SulfoniumChemistryElectrophileNucleophilePummerer rearrangementSulfurCationic polymerizationOrganic chemistryMedicinal chemistrySalt (chemistry)Acetic anhydrideCatalysisSulfur-Based Synthesis TechniquesOrganic Chemistry Cycloaddition ReactionsSynthesis and Properties of Aromatic Compounds