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

Shanghai Mio Chemical Co., Ltd

Contact:0086 21- 64401188-622

Address:16 Floor NO.2 Jiefang Building, No. 4855 Dushi Road, 201100 Shanghai, P.R.China
Shenyang NovPharm Technology Co., Ltd.

Contact:.+86-24-24165786

Address:Room 306, Hongjin Mansion, No. 36-1, Wanliutang Rd., Shenhe District, Shenyang, Liaoning, P.R.C.
Wuhan Benjamin Pharmaceutical Chemical Co.,Ltd

Contact:86-27-52341789

Address:Room 1518 B suite, optical valley time square, No 111 Guanshan Road, Hongshan District,Wuhan,Hubei Province,China.
SuZhou LaiTeou

Contact:+86-0512-88957371

Address:shanghai
ZHEJIANG SYNOSE TECH CO.,LTD.

website:https://www.synose.com/

Contact:86-579-82275537

Address:No.1958 Liyu Road , jinhua,zhejiang,China

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