TY - JOUR
T1 - The unexpected formation and structure of 4,6-dimethylthieno[3,4-c] thiophene-1(3H)-thione
AU - Tice, Nathan C.
AU - Peak, Sarah M.
AU - Parkin, Sean
PY - 2010
Y1 - 2010
N2 - The reaction of 2,5-dimethylthiophene-3,4-dicarboxaldehye (1) with excess Lawesson's Reagent afforded the unexpected 5,5-fused ring thienothione derivative, 4,6-dimethylthieno[3,4-c]thiophene-1(3H)-thione (2), in good yield (79%). The desired non-classical thiophene, 1,3-dimethylthieno[3,4-c]thiophene (3), was observed by GC/MS as a minor product (approximately 5%) along with thione 2. The thienothione 2 was characterized spectroscopically and its structure was confirmed by X-ray crystallography. The formation of compound 2 is proposed to occur through a 1,3-hydride shift.
AB - The reaction of 2,5-dimethylthiophene-3,4-dicarboxaldehye (1) with excess Lawesson's Reagent afforded the unexpected 5,5-fused ring thienothione derivative, 4,6-dimethylthieno[3,4-c]thiophene-1(3H)-thione (2), in good yield (79%). The desired non-classical thiophene, 1,3-dimethylthieno[3,4-c]thiophene (3), was observed by GC/MS as a minor product (approximately 5%) along with thione 2. The thienothione 2 was characterized spectroscopically and its structure was confirmed by X-ray crystallography. The formation of compound 2 is proposed to occur through a 1,3-hydride shift.
UR - http://www.scopus.com/inward/record.url?scp=79751490665&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79751490665&partnerID=8YFLogxK
U2 - 10.3987/COM-10-12023
DO - 10.3987/COM-10-12023
M3 - Article
AN - SCOPUS:79751490665
VL - 81
SP - 2229
EP - 2237
IS - 10
ER -