Chemistry of 2H‐thiopyran and derivatives I. 2H‐ versus 6H‐proton abstraction from 2H‐thiopyran

Abstract

Listen

Translate article

AbstractDepending on the nature of the base/solvent system deprotonation at carbon atoms 2 and 6 in 2H‐thiopyran 1 can be carried out specifically. Conversion of 6‐lithio‐2H‐thiopyran (4) into the charge‐delocalised species 2 takes place in the presence of diisopropylamine, probably via a process of proton donation and abstraction. Addition of hexamethylphosphoric triamide (HMPT) to the solution of 4 also gives rise to the formation of the thermodynamically more stable species 2.