SULFUR-TRIOXIDE SULFONATION OF DIPHENYL ETHER, DIPHENYL SULFIDE, DIBENZO[B,E][1,4]DIOXIN, AND XANTHENE

被引：1

作者：

CERFONTAIN, H

KOEBERGTELDER, A

VANLINDERT, HCA

BAKKER, BH

DEWIT, P

机构：

[1] Laboratory of Organic Chemistry, University of Amsterdam, 1018 WS Amsterdam

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1994年 / 97卷 / 1-4期

关键词：

SULFUR TRIOXIDE SULFONATION; DIPHENYL ETHER; DIPHENYL SULFIDE; DIBENZO[B,E][1,4]DIOXIN; XANTHENE;

D O I：

10.1080/10426509408020747

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The sulfur trioxide sulfonation of diphenyl ether (1), diphenyl sulfide (2), and the related tricyclic dibenzo[b,e][1,4]dioxin (3) and xanthene (4) has been studied. The substrates I and 2 both yield initially the 4-sulfonic acid derivative (4-S) and subsequently the 4,4'-S-2. In a large excess of 104.5 wt-% H2SO4 the further sulfonation of 1-4,4'-S-2 gave the 1-2,4,4'-S-3 and subsequently Some 1-2,4,2',4'-S-4. Sulfonation of the dibenzodioxin 3 with 4.0 mol-equiv. of SO3 gave the 2-S derivative, whereas with 12.0 mol-equiv. of SO3 a mixture of the 2,7-S-2 and 2,8-S-2 was obtained in yields of 57 and 43%, respectively. Sulfonation of xanthene (4) with 4.0 mol-equiv, of SO3 yielded the 2,7-S-2 derivative.

引用

页码：239 / 244

页数：6

共 50 条

[31] 11-R-dibenzo[b,e][1,4]diazepin-1-ones, the chemosensors for transition metal cations
I. E. Tolpygin
N. V. Mikhailenko
A. A. Bumber
E. N. Shepelenko
U. V. Revinsky
A. D. Dubonosov
V. A. Bren’
V. I. Minkin
[J]. Russian Journal of General Chemistry, 2012, 82 : 1243 - 1249
[32] 2,4-Diphenyl-4,5-dihydro-3H-pyrido[2,3-b][1,4]diazepine
Fun, Hoong-Kun
Yeap, Chin Sing
Hazra, Anita
Jana, Subrata
Goswami, Shyamaprosad
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1139 - U3094
[33] Geometric forms of 8-chloro-11-[4-(8-chloro-5H-dibenzo[b,e][1,4]diazepin-11-yl)piperazin-1-yl]-5H-dibenzo[b,e][1,4]-diazepine-acetone-pentane(2/1/1)
Capuano, Ben
Crosby, Ian T.
Fallon, Gary D.
Forsyth, Craig M.
Lloyd, Edward J.
Podloucka, Anna
Yuriev, Elizabeth
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O4034 - U2899
[34] 11H-dibenzo[b,e]azepines. Part 2. Synthesis of 10-15N-dibenzo[b,f] [1,4]oxazepine
Noskov V.G.
Kruglyak Yu.L.
Strukov O.G.
Kurochkin V.K.
[J]. Pharmaceutical Chemistry Journal, 1997, 31 (9) : 492 - 493
[35] CONFORMATIONS OF SOME SEMI-RIGID NEUROLEPTIC DRUGS .1. CRYSTAL-STRUCTURES OF LOXAPINE, CLOZAPINE, AND HUF-2046 MONOHYDRATE [2-CHLORO-11-(4-METHYLPIPERAZIN-1-YL)DIBENZO[B,F][1,4]OXAZEPINE, 8-CHLORO-11-(4-METHYLPIPERAZIN-1-YL)DIBENZO[B,E][1,4]DIAZEPINE, AND 2-CHLORO-11-(4-METHYLPIPERAZIN-1-YL)DIBENZO[B,E][1,4]DIAZEPINE MONOHYDRATE
PETCHER, TJ
WEBER, HP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (12): : 1415 - 1420
[36] SYNTHESIS AND NEUROLEPTIC EFFECTS OF NEW 11-SUBSTITUTED 5H-DIBENZO[B,E][1,4]DIAZEPINES
SKOLDINOV, AP
RAYEVSKII, KS
LIKHOSHERSTOV, AM
STAVROVSKAJA, AW
RUGER, C
ROSTOCK, A
ROHNERT, H
[J]. PHARMAZIE, 1984, 39 (12): : 812 - 813
[37] Palladium-mediated approach to dibenzo[b,e][1,4]diazepines and benzopyrido-analogues.: An efficient synthesis of tarpane
Beccalli, EM
Broggini, G
Paladino, G
Zoni, C
[J]. TETRAHEDRON, 2005, 61 (01) : 61 - 68
[38] SULFONATION OF 1,2-(METHYLENEDIOXY)BENZENE, 1,2-(ETHYLENEDIOXY)BENZENE, 2-METHYLANISOLE, 2,3-DIHYDROBENZOFURAN, CHROMANE, BENZO-15-CROWN-5 AND DIBENZO-30-CROWN-10 IN CONCENTRATED SULFURIC-ACID AND WITH SULFUR-TRIOXIDE
ANSINK, HRW
CERFONTAIN, H
[J]. RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1989, 108 (11): : 395 - 403
[39] PHARMACOLOGY OF 8-CHLORO-11-(4-METHYL-1-PIPERAZINYL))-5H-DIBENZO[B,E][1,4]DIAZEPINE (CLOZAPINE)
STILLE, G
LAUENER, H
EICHENBERGER, E
[J]. FARMACO-EDIZIONE PRATICA, 1971, 26 (10): : 603 - +
[40] Synthesis of 11-(Piperazin-1-yl)-5H-dibenzo[b,e] [1,4]diazepine on Kilo Scale
Kalhapure, Rahul S.
Patil, Bhushan P.
Jadhav, Mahantesh N.
Kawle, Laxmikant A.
Wagh, Sanjay B.
[J]. E-JOURNAL OF CHEMISTRY, 2011, 8 (04) : 1747 - 1749

← 1 2 3 4 5 →