The Reaction of Thiophene 1,1-Dioxide With Haloform-Sodium Hydroxide Under Phase-Transfer Catalysis

1989 ◽  
Vol 42 (8) ◽  
pp. 1307 ◽  
Author(s):  
BR Dent ◽  
GJ Gainsford
Keyword(s):  
Low Temperature ◽  
Sodium Hydroxide ◽  
Good Yield ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Structural Data ◽  
X Ray ◽  
Benzyltriethylammonium Chloride

3,4-Dibromotetrahydrothiophen 1,1-dioxide (2) reacts in the reagent system chloroformaqueous sodium hydroxide-benzyltriethylammonium chloride to give 3-dichloromethylene-2,3-dihydrothiophen 1,1-dioxide (6a), for which low-temperature X-ray structural data are presented. Bromoform may be substituted for chloroform to give the corresponding dibromomethylene compound (6b) in good yield.

scholarly journals Synthesis, structure, and first reactions of a new class of thiacyclophanes

2017 ◽  
Vol 95 (3) ◽  
pp. 278-285 ◽  
Author(s):  
Arunachalam Kannan ◽  
Henning Hopf ◽  
Ina Dix ◽  
Peter G. Jones ◽  
Ludger Ernst
Keyword(s):  
Spectroscopic Data ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
X Ray ◽  
Flash Vacuum Pyrolysis ◽  
New Class ◽  
Product Mixture ◽  
Vacuum Pyrolysis ◽  
Molecular Bridge ◽  
Meta Isomer

In our effort to prepare [m.n]cyclophanes carrying functional groups in their molecular bridges, the thiacyclophanes 14, 19, 20, and 21 have been prepared by simple routes from the pseudo-gem dibromide 10a and the corresponding bis-thiol 10b. The triply-bridged bis-thia-cyclophanes 14, and 19-21 were characterized by their spectroscopic data as well as by X-ray structural analyses. The meta-isomer 20 was oxidized to the bis-sulfone 23, which on flash vacuum pyrolysis (FVP) yielded a product mixture presumably containing the hydrocarbon 26 with a cleaved molecular bridge. Subjecting 23 to Ramberg-Bäcklund conditions (CCl4, NaOH, phase transfer catalysis) provided the chloride 24 in poor yield (9%), a [2.2]paracyclophane in which the new molecular bridge is fully conjugated.

Solid - liquid phase transfer catalysis using solid sodium hydroxide in preparative ethers synthesis

2010 ◽  
Vol 89 (6) ◽  
pp. 421-426
Author(s):  
H. Jm. Dou ◽  
B. Delfort ◽  
P. Hassanaly ◽  
R. Gallo ◽  
J. Kister
Keyword(s):  
Liquid Phase ◽  
Sodium Hydroxide ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Solid Liquid

Regiospecific Synthesis of Three Quercetin O-β-Glucosides of N-Acetylglucosamine

2018 ◽  
Vol 42 (4) ◽  
pp. 189-193
Author(s):  
Zhiling Cao ◽  
Jing Chen ◽  
Dandan Zhu ◽  
Zongnan Yang ◽  
Wenqi Teng ◽  
...  
Keyword(s):  
Good Yield ◽  
Phase Transfer Catalysis ◽  
Phase Transfer

The regiospecific synthesis of three quercetin O-β-glucosides of N-acetylglucosamine has been achieved in good yield. Selective di-and tri- O-benzylation of quercetin followed by O-glycosylation with 2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-α-D-glucopyranosyl chloride under phase-transfer catalysis conditions yielded, after deacetylation and debenzylation, 3-, 3′- and 4′-glycosylated quercetin.

ChemInform Abstract: The Reaction of Thiophene 1,1-Dioxide with Haloform-Sodium Hydroxide Under Phase-Transfer Catalysis.

ChemInform ◽  
1989 ◽  
Vol 20 (48) ◽  
Author(s):  
B. R. DENT ◽  
G. J. GAINSFORD
Keyword(s):  
Sodium Hydroxide ◽  
Phase Transfer Catalysis ◽  
Phase Transfer

The regioselective α-alkylation of the benzophenone imine of glycinamide, alaninamide, and related derivatives

2006 ◽  
Vol 84 (10) ◽  
pp. 1301-1312 ◽  
Author(s):  
Martin J O'Donnell ◽  
Jeremy D Keeton ◽  
Vien Van Khau ◽  
John C Bollinger
Keyword(s):  
Crystal Structures ◽  
Schiff Bases ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Ion Pair ◽  
X Ray ◽  
Disubstituted Product

The benzophenone imine of glycinamide was alkylated using ion pair extraction (RX, 10% aq. NaOH, Bu4NHSO4 (1 equiv.), CH2Cl2, rt) to give the α-monosubstituted products, which were then alkylated a second time using stronger basic conditions (KO-t-Bu, THF, 0 °C, RX). Crystal structures of the Schiff bases of glycinamide, an α-monosubstituted and an α,α-disubstituted product were reported.Key words: benzophenone imines, Schiff bases, alkylation, ion pair extraction (IPE), phase-transfer catalysis (PTC), anhydrous base, X-ray crystal structures.

Regioselective synthesis of biologically interesting pentacyclic polyheterocycles by sequential thio-Claisen and AlCl3 catalyzed oxy-Claisen rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-1-phenyl-1,8-naphthyridin-2(1H)-one

2006 ◽  
Vol 84 (12) ◽  
pp. 1632-1639 ◽  
Author(s):  
K C Majumdar ◽  
R Islam
Keyword(s):  
Lewis Acid ◽  
Claisen Rearrangement ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Acid Catalyst ◽  
Sigmatropic Rearrangement ◽  
Regioselective Synthesis ◽  
X Ray ◽  
Lewis Acid Catalyst ◽  
Acid Catalyzed

A number of 4-aryloxymethyl-6-phenyl-2H-thiopyrano[3,2-c][1,8]naphthyridin-5(6H)-ones were regio selectively synthesized in 82%–95% yields by the thermal Claisen rearrangement of 4-(4′-aryloxybut-2′-ynylthio)-1-phenyl-[1,8]naphthyridin-2(1H)-ones. These products were then subjected to a second Claisen rearrangement in the presence of a Lewis acid catalyst, anhyd. AlCl3, to give hitherto unreported pentacyclic heterocycles in 75%–90% yields. The same final products were also obtained in low yield upon refluxing 4-aryloxymethyl-6-phenyl-2H-thio pyrano-[3,2-c][1,8]naphthyridin-5(6H)-ones in N,N-diethyl aniline for 12–14 h. This method was found to be more effective than thermal Claisen rearrangement.Key words: [3,3] sigmatropic rearrangement, regioselective synthesis, phase transfer catalysis, sequential Claisen rearrangement, Lewis acid catalyzed Claisen rearrangement, single crystal X-ray.

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