[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

• conformationally restricted and freely interconverting thia-bridged systems have been identified [7][8][9][10][11][12][13][14][15][16][17]. Cyclophanes incorporating simple heteronuclei such as furan, thiophene, pyridine, pyridazine and benzothiazole are abundantly known [1][2][3]. Despite the known structural

Enantiospecific synthesis of [2.2]paracyclophane- 4-thiol and derivatives

• Gareth J. Rowlands and
• Richard J. Seacome

Beilstein J. Org. Chem. 2009, 5, No. 9, doi:10.3762/bjoc.5.9

• describes a simple route to enantiomerically enriched [2.2]paracyclophane-4-thiol via the stereospecific introduction of a chiral sulfoxide to the [2.2]paracyclophane skeleton. The first synthesis of an enantiomerically enriched planar chiral benzothiazole is also reported. Keywords: heterocycle; [2.2

• demonstrated in the synthesis of the planar chiral benzothiazole (Rp)-10 (Scheme 2). Benzothiazoles are important heterocycles having found use as dyes, pharmaceuticals and ligands in catalysis [42]. Planar chiral heterocycles are still rare but show considerable potential as probes in stereocontrolled

• has the potential to produce a wide-range of thiol derivatives and this has permitted the first synthesis of a planar chiral benzothiazole, [2.2](4,7)benzo[d]thiazoloparacyclophane. The use of these thiols in asymmetric synthesis is currently being investigated and will be reported in due course