Optically active (R)-(+)-1,1'-spirobi[3H-2,1-benzoxathiol]-3-one (R)-(+)-5, the (R)-(+) and (S)-(-) enantiomers of spiro[3H-2,1-benzoxathiol-1,1'-naphtho[1,8-d,e]3H-2,1-oxathiin-3-one] (R)-(+)-8 and (S)-(-)-8, and (S)-(+)-spiro[3H-2,1-benzoxathiol-3-one-1,1'-naphtho[1,8-d,e]-3H-2,1-oxathiine] (S)-(+)-10 all belonging to the class of diaryl(acyloxy)-(alkoxy)spiro-λ4-sulfanes (spirosulfuranes) were prepared by dehydration of the optically active diaryl sulfoxides (R)-(+)-4, (R)-(-)-7, (S)-(+)-7, and (S)-(+)-9, respectively, all of them carrying reactive CH2OH and COOH substituents. (R)-(+)-5H,7H-dibenzo[c,f]-1,5-oxathiocin-5-one 12-oxide (R)-(+)-6, a sulfoxide-lactone isomer of spiro-λ4-sulfane (R)-(+)-5 was also obtained from (R)-(+)-4 by dehydration. The molecular structures including the absolute configurations were determined for (R)-(+)-5, (R)-(+)-6 and (R)-(+)-8 by X-ray diffraction method. Relevant bond length and angle data are listed. Sulfur configurations, solid-state conformations and a stereospecific pathway for the dehydration of sulfoxides are discussed in detail.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry