[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis

• Sabir H. Mashraqui,
• Yogesh Sanghvikar,
• Shailesh Ghadhigaonkar,
• Sukeerthi Kumar,
• Auke Meetsma and
• Elise Trân Huu Dâu

Beilstein J. Org. Chem. 2009, 5, No. 74, doi:10.3762/bjoc.5.74

• Institut de Chimie des Substances Naturelles, C.N.R.S., 91190 Gif-sur-Yvette, France 10.3762/bjoc.5.74 Abstract The synthesis of [3.3]dithia-bridged cyclophanes 7, 9 and 11 incorporating a fused heterocycle, thieno[2,3-b]thiophene is described. The structures are established by 1H NMR analysis and, in the

• ]dithia-bridged cyclophanes; dynamic NMR analysis; thieno[2,3-b]thiophene; X-ray crystal structure; Introduction The synthesis, molecular structures and conformational dynamics of short-bridged cyclophanes continue to engage interest in supramolecular chemistry [1][2][3][4]. The study of the

• diversity and complexity of cyclophanes, it is surprising that cyclophanes featuring fused heteronuclei have scarcely been studied [18][19][20]. Lately, we have been exploiting the thieno[2,3-b]thiophene ring, a fused heterocycle towards creating potentially interesting intramolecular charge transfer [21