Generation and Rearrangemnent of C2-Symmetric Chiral Allyl Anions derived from Dibenzo- and 1,1'-Dinaphtho-2,2'-dithiopropenes

Article abstract of DOI:10.1016/S0040-4039(00)92304-9

The allyl anions generated from 4H-dinaphtho<2,1-f:1',2'-h><1,5>dithionin (6) and 2-ethenyl-dinaphtho<2,1-d:1',2'-f><1,3>dithiepin (8) rearranged both to the thiolate 10 which further reacted with water or methyl iodide to afford 9 or 12 respectively.A similar behavior was exhibited by the anion of 4H-dibenzo<1,5>dithionin. Key words: 1,3-Dithioallyl anions, dibenzo-2,2'-dithiol, 1,1'-dinaphtho-2,2'-dithiol, atropisomeric sulfur reagents, C₂-symmetric chiral reagents.