Synthesis of 1,4-dithiins from pentathiepins.
Fused aromatic and heterocyclic 1,2,3,4,5-pentathiepins react with triphenylphosphine and alkynes bearing electron-withdrawing groups to give the corresponding 1,4-dithiins in high yields. Unsymmetrical alkynes add regioselectively to afford products in agreement with the electron distribution in a proposed reaction intermediate. A mechanism for these reactions is proposed.
Amelichev
Stanislav A
SA
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, 119991 Moscow, Russia.
Konstantinova
Lidia S
LS
Obruchnikova
Natalia V
NV
Rakitin
Oleg A
OA
Rees
Charles W
CW
D006571:Heterocyclic Compounds / Q000138:chemical synthesis*
D006571:Heterocyclic Compounds