Synthesis and acidity of conformationally constrained 1,3 oxathiane S oxides
Abstract Conformationally constrained 5 tert butyl 1,3 oxathiane was synthesized and oxidation led to the diastereoisomeric sulfoxides and the respective sulfone. Stereoelectronic effects are discussed for these compounds and their corresponding 2 carbanions. p K a values are calculated for these compounds and compared with the respective 1,3 dithiane derived sulfide, the sulfoxides, and the sulfone.