Odorless Thioacetalization Reagent 2‐[1,3]Dithian‐2‐Ylidene‐3‐Oxo‐Butanamide and Its Chemoselectivity

Abstract

2‐[1,3]Dithian/dithiolan‐2‐ylidene‐3‐oxo‐butanamide 2a/2b were synthesized and investigated in the thioacetalization reaction of aldehydes/ketones 3. The experiments revealed that 2a could be used as a nonthiolic, odorless 1,3‐propanedithiol equivalent in the conversion of aldehydes/ketones into the corresponding dithianes 4, however, 2b was less effective. Moreover, the chemoselectivity of the thioacetalization of 3 in the presence of 2a is discussed.

Keywords:

• Carbonyl compounds
• Chemoselectivity
• α‐oxo ketene dithioacetals
• 1,3‐propanedithiol equivalent

Acknowledgments

This research was supported by NNSFC (20272008) and the Key Project of Chinese Ministry of Education (03059).