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Sulfur-rich heterocycles from 2-metalated benzo[b]thiophene and benzo[b]furan: synthesis and structure



Sulfur-rich heterocycles from 2-metalated benzo[b]thiophene and benzo[b]furan: synthesis and structure



Journal of Organic Chemistry 67(17): 6220-6223



The reaction of 2-lithiated benzo[b]thiophene with 8 equiv of elemental sulfur was found to give pentathiepino[6,7-b]benzo[d]thiophene. In contrast, treatment of 2-lithiated benzo[b]furan with sulfur under similar conditions produced the interesting ring system bis(benzo[4,5]furo)[2,3-e:3',2'-g][1,2,3,4]tetrathiocine. Both of these new cyclic polysulfides were studied by X-ray crystallography. Two polymorphic forms of pentathiepino[6,7-b]benzo[d]thiophene were found, displaying similar conformations but different packing schemes, which was also evident from powder diffraction data.

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Accession: 047480980

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PMID: 12182664

DOI: 10.1021/jo0257086


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