Optimal synthesis and sulfonylation mechanism of a novel polyhedral oligomeric octadiphenylsulfonylsilsesquioxane

Ziqian Li; Rongjie Yang

doi:10.6023/cjoc201405022

Optimal synthesis and sulfonylation mechanism of a novel polyhedral oligomeric octadiphenylsulfonylsilsesquioxane

Ziqian Li
, Rongjie Yang^*

^*Corresponding author for this work

Beijing Institute of Technology

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

Abstract

Octadiphenylsulfonylsilsesquioxane (ODPSS) was synthesized through sulfonylation of octaphenylsilsesquioxane (OPS) with benzenesulfonyl chloride and the AlCl₃ catalyst in dichloromethane (CH₂Cl₂). By changing the solvent, catalyst, reaction time and molar ratio of reactants, the optimal reaction conditions were determined. It was found that OPS could be completely converted to ODPSS with a high yield. The product ODPSS was identified by FTIR, MALDI-TOF MS, ¹H NMR, ¹³C NMR, ²⁹Si NMR and elemental analysis. The reaction mechanism was analyzed and a sulfonylation model of OPS was established.

Original language	English
Pages (from-to)	2338-2344
Number of pages	7
Journal	Chinese Journal of Organic Chemistry
Volume	34
Issue number	11
DOIs	https://doi.org/10.6023/cjoc201405022
Publication status	Published - 1 Nov 2014
Externally published	Yes

Keywords

Friedel-Crafts sulfonylation
Octadiphenylsulfonylsilsesquioxane
Octaphenylsilsesquioxane

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title = "Optimal synthesis and sulfonylation mechanism of a novel polyhedral oligomeric octadiphenylsulfonylsilsesquioxane",

abstract = "Octadiphenylsulfonylsilsesquioxane (ODPSS) was synthesized through sulfonylation of octaphenylsilsesquioxane (OPS) with benzenesulfonyl chloride and the AlCl3 catalyst in dichloromethane (CH2Cl2). By changing the solvent, catalyst, reaction time and molar ratio of reactants, the optimal reaction conditions were determined. It was found that OPS could be completely converted to ODPSS with a high yield. The product ODPSS was identified by FTIR, MALDI-TOF MS, 1H NMR, 13C NMR, 29Si NMR and elemental analysis. The reaction mechanism was analyzed and a sulfonylation model of OPS was established.",

keywords = "Friedel-Crafts sulfonylation, Octadiphenylsulfonylsilsesquioxane, Octaphenylsilsesquioxane",

author = "Ziqian Li and Rongjie Yang",

note = "Publisher Copyright: {\textcopyright} 2014 Chinese Chemical Society \& SIOC, CAS.",

year = "2014",

month = nov,

day = "1",

doi = "10.6023/cjoc201405022",

language = "English",

volume = "34",

pages = "2338--2344",

journal = "Chinese Journal of Organic Chemistry",

issn = "0253-2786",

publisher = "Science Press",

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TY - JOUR

T1 - Optimal synthesis and sulfonylation mechanism of a novel polyhedral oligomeric octadiphenylsulfonylsilsesquioxane

AU - Li, Ziqian

AU - Yang, Rongjie

PY - 2014/11/1

Y1 - 2014/11/1

N2 - Octadiphenylsulfonylsilsesquioxane (ODPSS) was synthesized through sulfonylation of octaphenylsilsesquioxane (OPS) with benzenesulfonyl chloride and the AlCl3 catalyst in dichloromethane (CH2Cl2). By changing the solvent, catalyst, reaction time and molar ratio of reactants, the optimal reaction conditions were determined. It was found that OPS could be completely converted to ODPSS with a high yield. The product ODPSS was identified by FTIR, MALDI-TOF MS, 1H NMR, 13C NMR, 29Si NMR and elemental analysis. The reaction mechanism was analyzed and a sulfonylation model of OPS was established.

AB - Octadiphenylsulfonylsilsesquioxane (ODPSS) was synthesized through sulfonylation of octaphenylsilsesquioxane (OPS) with benzenesulfonyl chloride and the AlCl3 catalyst in dichloromethane (CH2Cl2). By changing the solvent, catalyst, reaction time and molar ratio of reactants, the optimal reaction conditions were determined. It was found that OPS could be completely converted to ODPSS with a high yield. The product ODPSS was identified by FTIR, MALDI-TOF MS, 1H NMR, 13C NMR, 29Si NMR and elemental analysis. The reaction mechanism was analyzed and a sulfonylation model of OPS was established.

KW - Friedel-Crafts sulfonylation

KW - Octadiphenylsulfonylsilsesquioxane

KW - Octaphenylsilsesquioxane

UR - https://www.scopus.com/pages/publications/84916894827

U2 - 10.6023/cjoc201405022

DO - 10.6023/cjoc201405022

M3 - Article

AN - SCOPUS:84916894827

SN - 0253-2786

VL - 34

SP - 2338

EP - 2344

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 11

ER -

Optimal synthesis and sulfonylation mechanism of a novel polyhedral oligomeric octadiphenylsulfonylsilsesquioxane

Abstract

Keywords

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