Synthesis and stereochemistry of 1H,5H-naphtho[1,8-ef][1,3]dithiocine 2-oxides

Abstract

3-Substituted 1H,5H-naphtho[1,8-ef][1,3]dithiocines (R = H, Me, Ph, t-Bu) were oxidized with m-chloroperoxybenzoic acid to the corresponding 2-oxides having trans configuration (R ≠ H). According to the 1H and 13C NMR data (including NOESY experiments), the disubstituted compounds at room temperature exist in a boat conformation with equatorial orientation of the substituent on C3 and oxygen atom on S 2. The compound with no substituent on C3 gives rise to a mixture of boat conformers with axial and equatorial sulfoxide oxygen atoms at a ratio of 83:17. © 2005 Pleiades Publishing, Inc