Novel Electrophilic Species Equivalent to α-Keto Cations. Reactions of O,O-Diprotonated Nitro Olefins with Benzenes Yield Arylmethyl Ketones

DOI: 10.1021/jo00265a001

Source and publish data:

Journal of Organic Chemistry p. 733 - 734 (1989)

Update date:2022-08-16

Topics:

Authors:

Okabe, Kazuaki

Ohwada, Tomohiko

Ohta, Toshiharu

Shudo, Koichi

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

Article abstract of DOI:10.1021/jo00265a001

The N,N-dihydroxyiminium carbenium ions formed by O,O-diprotonation of nitro olefins in a strong acid, trifluoromethanesulfonic acid (TFSA), are discrete and novel dipositively charged species.The dications formed from α-substitited nitroethylenes are reactive electrophiles to give α-arylated ketones in high yields.This constitutes a versatile synthetic method for the preparation of α-arylated ketones, which are difficult to synthesize by the conventional Friedel-Crafts reactions.

Full text of DOI:10.1021/jo00265a001

Products guided by the article

Product name:1-PHENYL-2-BUTANONE

Cas No:1007-32-5

R&D Labs maybe for 1007-32-5

Valiant Fine Chemicals Co., Ltd.

Contact:+86 535 6101878/6374484

Address:11 Wuzhishan Rd.,YTETDZ,Yantai,264006,Shandong,China
Shanghai Korey Pharm Co.,Ltd.(expird)

Contact:021-61840961 021-61840962

Address:No.157,Zhuguang Rd, Qingpu, Shanghai, China
Arromax Pharmatech Co.,Ltd

website:http://www.arromax.com

Contact:+86-0512-62959601 skype:aimmezhang

Address:Suite 401, Bldg A3, 218 Xinghu St.Suzhou Industrial Park 215123, P.R. China
HAINAN JINYING IMPORT AND EXPORT CO. LTD

Contact:+86-898-32875423

Address:A SECTION 19TH FL, TIMES SQUARE, NO.2 GUO MAO AVENUE HAIKOU, HAINAN, P. R. OF CHINA
Wuhan Konberd Biotech Co., Ltd.

Contact:+86-27-87205925

Address:NO.666, Gaoxin Road, Eastlake High-tech zone

Relevant to this article

Synthesis of 2-N-substituted benzothiazoles via domino condensation-hetero cyclization process, mediated by copper oxide nanoparticles under ligand-free conditions

Doi:10.1016/j.tetlet.2012.03.012
(2012)
Syntheses and properties of nine-ring-fused linear thienoacenes

Doi:10.1021/jo4025607
(2014)
Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

Doi:10.1021/acscatal.6b01261
(2016)
Doi:10.1002/hlca.19650480821
(1965)
Thiols make for better catalysts: Au nanoparticles supported on functional SBA-15 for catalysis of Ullmann-type homocouplings

Doi:10.1039/c7cc06146c
(2017)
A Principle for Highly Active Metal Oxide Catalysts via NaCl-Based Solid Solution

Doi:10.1016/j.chempr.2020.04.003
(2020)

Article Doi