TY - JOUR
T1 - Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction
AU - Liu, Shuli
AU - Huang, Chengting
AU - Zhang, Jing
AU - Tian, Siyu
AU - Li, Chang
AU - Fu, Nina
AU - Wang, Lianhui
AU - Zhao, Baomin
AU - Huang, Wei
N1 - Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/5/26
Y1 - 2019/5/26
N2 - We present herein a strategy towards the straightforward synthesis of a novel sulfur-hybridized pyracylene, tetraceno[5,6-bc:11,12-b'c']dithiophene (TDT) derivatives, via 2-fold FeCl3-mediated Scholl reaction. Surprisingly, the substituents on the precursors will guide the synthetic route, when the substituents were bromo- or phenyl-, quantitatively debromination or phenyl ring shift mediated rearrangement were observed respectively, the rearrangement products were identified by the HR-Mass and 2D NMR analyses. Additionally, a retrosynthetic method was adopted to confirm the unexpected reaction results in rearrangement of Scholl reaction.
AB - We present herein a strategy towards the straightforward synthesis of a novel sulfur-hybridized pyracylene, tetraceno[5,6-bc:11,12-b'c']dithiophene (TDT) derivatives, via 2-fold FeCl3-mediated Scholl reaction. Surprisingly, the substituents on the precursors will guide the synthetic route, when the substituents were bromo- or phenyl-, quantitatively debromination or phenyl ring shift mediated rearrangement were observed respectively, the rearrangement products were identified by the HR-Mass and 2D NMR analyses. Additionally, a retrosynthetic method was adopted to confirm the unexpected reaction results in rearrangement of Scholl reaction.
KW - Debromination
KW - Fused ring aromatics
KW - Rearrangement
KW - Scholl reaction
KW - Sulfur-hybridized pyracylene
UR - http://www.scopus.com/inward/record.url?scp=85065797279&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201900344
DO - 10.1002/ejoc.201900344
M3 - 文章
AN - SCOPUS:85065797279
SN - 1434-193X
VL - 2019
SP - 3061
EP - 3070
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 19
ER -