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Paper | Special issue | Vol 50, No. 1, 1999, pp.103-108
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)7
Synthesis with Bis(o-mercapto)phenyl Sulfide: An Easy Access to Sulfurcontaining 16-Membered Heterocycles

Juzo Nakayama,* Sanae Tanaka, Yoshiaki Sugihara, and Akihiko Ishii

*Department of Chemistry, Faculty of Science, Saitama University, Saitama, Saitama 338-8570, Japan

Abstract

Condensations of bis(o-mercaptophenyl) sulfide (4) with paraformaldehyde or diiodomethane in moderately concentrated solutions gave 28-49% yield of a 1:1 condensation product, dibenzotrithiocin (5b), and 6-10% yield of a 2:2 condensation product (6b) with a 16-membered ring, whereas condensation of 4 with diiodomethane in a dilute solution gave 5b in 90% yield. Condensations of 4 with 1,1’-carbonyl- and 1,1’-thiocarbonyl-diimidazoles gave 2:2 condensation products (6c) and (6d) as the practically sole product in 79 and 57% yields, respectively, thus providing a convenient synthesis of 16-membered heterocycles containing 6 sulfur atoms in the ring.