3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of Cα-Si Bond

被引：23

作者：

Das, Soumyajit ^{[1
]}

Dutta, Pradip Kumar ^{[1
]}

Panda, Snigdha ^{[1
]}

Zade, Sanjio S. ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res, Dept Chem Sci, Nadia 741252, W Bengal, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 14期

关键词：

HIGH-CONTRAST RATIO; ELECTROCHEMICAL POLYMERIZATION; ELECTROCHROMIC POLYMERS; BUILDING-BLOCK; EDOT; SELENOPHENE; METHYLENEDIOXYHETARENES; DERIVATIVES; PEDOT;

D O I：

10.1021/jo100756k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to synthesize EDOT and EDOS from a common precursor 5 is reported. The method involves zirconocene dichloride mediated reaction of a common diyne 5 followed by treatment with disulfur dichloride (S2Cl2) and in situ prepared selenium dichloride (SeCl2). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.

引用

页码：4868 / 4871

页数：4

共 53 条

[1]

[Anonymous], 1998, Electronic materials: the oligomer approach

[2]

[Anonymous], NBO 3 1

[3] Synthesis of 3,4-ethylenedioxyselenophene (EDOS):: A novel building block for electron-rich π-conjugated polymers [J].

Aqad, E ;

Lakshmikantham, MV ;

Cava, MP .

ORGANIC LETTERS, 2001, 3 (26) :4283-4285

[4] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[5] Efficient synthesis of 3,4-ethylenedioxythiophenes (EDOT) by Mitsunobu reaction [J].

Caras-Quintero, D ;

Bäuerle, P .

CHEMICAL COMMUNICATIONS, 2002, (22) :2690-2691

[6] A facile synthesis of 3,4-dialkoxythiophenes [J].

Coffey, M ;

McKellar, BR ;

Reinhardt, BA ;

Nijakowski, T ;

Feld, WA .

SYNTHETIC COMMUNICATIONS, 1996, 26 (11) :2205-2212

[7] METHYLENEDIOXYHETARENES, .1. PREPARATION OF 3,4-METHYLENEDIOXYTTHIOPHENE METHYLENEDIOXYFURAN, AND METHYLENEDIOXYPYRROLE DERIVATIVES [J].

DALLACKER, F ;

MUES, V .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (02) :569-575

[8] METHYLENEDIOXYHETARENES .2. REACTIONS OF DIETHYL 3,4-METHYLENEDIOXY-2,5-THIOPHENEDICARBOXYLATE [J].

DALLACKER, F ;

MUES, V .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (02) :576-581

[9] Poly(cyclopenta[c]selenophene): a new polyselenophene [J].

Das, Soumyajit ;

Zade, Sanjio S. .

CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1168-1170

[10] SOME DERIVATIVES OF 3,4-DIOXYTHIOPHENE [J].

FAGER, EW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (12) :2217-2218

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