Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction

Shuli Liu; Chengting Huang; Jing Zhang; Siyu Tian; Chang Li; Nina Fu; Lianhui Wang; Baomin Zhao; Wei Huang

doi:10.1002/ejoc.201900344

Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction

Shuli Liu, Chengting Huang, Jing Zhang, Siyu Tian, Chang Li, Nina Fu, Lianhui Wang, Baomin Zhao, Wei Huang

Institute of Flexible Electronics

Nanjing University of Posts and Telecommunications

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3061-3070
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201900344
State	Published - 26 May 2019

Keywords

Debromination
Fused ring aromatics
Rearrangement
Scholl reaction
Sulfur-hybridized pyracylene

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10.1002/ejoc.201900344

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title = "Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction",

abstract = "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.",

keywords = "Debromination, Fused ring aromatics, Rearrangement, Scholl reaction, Sulfur-hybridized pyracylene",

author = "Shuli Liu and Chengting Huang and Jing Zhang and Siyu Tian and Chang Li and Nina Fu and Lianhui Wang and Baomin Zhao and Wei Huang",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/ejoc.201900344",

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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

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

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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 -

Synthesis of Sulfur-Hybridized Pyracylene and the Unexpected Phenyl Shift Mediated Rearrangement of Scholl Reaction

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Keywords

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