REACTIVITIES OF HETEROAROMATIC CATIONS CONTAINING A GROUP VIB ELEMENT IN NUCLEOPHILIC REACTIONS. REACTIONS OF 9-PHENYL-XANTHYLIUM, -THIOXANTHYLLIUM, AND -SELENOXANTHYLIUM SALTS WITH AMINES, SODIUM PHENOLATE, AND SODIUM BENZENETHIOLATE

DOI: 10.1039/P19880002271

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2271 - 2276 (1988)

Update date:2022-08-04

Topics: Amines

Authors:

Hori, Mikio

Kataoka, Tadashi

Shimizu, Hiroshi

Hsu, Chen Fu

Hasegawa, Yukio

Eyama, Noriko

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19880002271

Reactions of 9-phenylchalcogenoxanthyllium salts (1a-c) with some nucleophiles have been examined in order to find the differences in reactivity in nucleophilic reactions.The chalcogenoxanthylium salts (1a-c) react with aniline in ether to give 9-anilino-9-phenylchalcogenoxanthenes (7a-c).However, in acetonitrile the xanthylium salt (1a) affords N,4-bis(9-phenylxanthen-9-yl)aniline (9a) together with the anilinoxanthene (7a) (at room temperature) or 9-(p-aminophenyl)-9-phenylxanthene (8a) (at reflux) and the sulphur (1b) and the selenium derivative (1c) affords only the anilino derivatives (7b,c), respectively.In the reactions with sodium phenolate, the thioxanthylium salt (1b) gave 9-phenoxy-9-phenylthioxanthene (13b), whereas the oxygen (1a) and the selenium congener (1c) gave O,4-bis(9-phenylchalcogenoxanthen-9-yl)phenols (15a,c) together with the 9-phenoxy derivatives (13a,c), respectively.The results show that the thioxanthylium salt (1b) gave the products formed on attack by the heteroatom of the ambident nucleophiles and the ratio of the carbon attack increased in the order (1a) > (1c) > (1b).This difference would be attributable to the properties of carbocations at the 9-position in the heteroaromatic cations (1a-c).

Full text of DOI:10.1039/P19880002271

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:9-phenyl-9-(phenylthio)-thioxanthene

Cas No:116905-86-3

R&D Labs maybe for 116905-86-3

Henan Harvest Chem Co., Ltd

Contact:+86-371-86058576

Address:NO.32, Jingsan Road, Zhengzhou, China
TIANJIN FESTO CHEMICAL CO.,LTD(expird)

Contact:86-22-25814570

Address:No.12th,5th Ave.,TEDA,Tianjin,China
RongCheng K&S Chemical Co.,Ltd

Contact:0631-7336369

Address:rongcheng ,shandong province china
Pengchen New Material Technology Co., Ltd.

Contact:+86-512-63680537

Address:99.6 km of national road 318, Meiyan Community,Pingwang Town, Wujiang District, Suzhou 215225
Molobelamltrading

Contact:27-792-602929

Address:SIDNEY MUFAMADI STREET 009949 X44 0700 POLOKWANE,LIMPOPO

Relevant to this article

Doi:10.1039/jr9510002462
(1951)
SYNTHESIS AND PSYCHOPHARMACOLOGICAL ACTIVITY OF BENZHYDRYL GLYCINE DERIVATIVES

Doi:10.1007/BF00758310
(1989)
2-Amino-5-aryl-pyridines as selective CB₂ agonists: Synthesis and investigation of structure-activity relationships

Doi:10.1016/j.bmcl.2009.10.041
(2009)
Rotaxanes of a macrocyclic ferrocenophane with dialkylammonium axle components

Doi:10.1039/b907417a
(2009)
Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives

Doi:10.1021/jm900723w
(2010)
1-PHOSPHA-1,2-BUTADIENE - 1-PHOSPHA-1,2,3-BUTATRIENE

Doi:10.1016/0040-4039(88)85051-2
(1988)

Article Doi