Retentive Solvolysis. Part 12. Mechanism of the Reaction of Optically Active 1-(p-Methoxyphenyl)ethyl Trifluoroacetate with Phenol and Metanol in Benzene and Cyclohexane

DOI: 10.1039/P29800000842

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 842 - 848 (1980)

Update date:2022-08-17

Topics:

Authors:

Okamoto, Kunio

Takeuchi, Ken'ichi

Inoue,Takeshi

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

Article abstract of DOI:10.1039/P29800000842

The rate, product distribution, and stereochemical course for the reactions of 0.05-0.1M-1-(p-methoxyphenyl)ethyl trifluoroacetate (1) with methanol and phenol have been investigated in benzene or cyclohexane as solvent at 25.0 deg C.Below 1E-3M-methanol or -phenol the total kinetic order is two overall .The rates are virtually independent of the pyridine used to bind the trifluoroacetic acid produced.The major product from the phenol reaction, 1-(p-methoxyphenyl)ethyl phenyl ether, shows net retention (6-9percent) of configuration along with predominant racemization.In addition, the methyl ether product from the methanol reaction also undergoes net retention (24percent with 0.2M-methanol).The formation of the ethers with net retention of configuration can be accounted for by an intermolecular S_Ni mechanism.

Full text of DOI:10.1039/P29800000842

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

View Article Online

Products guided by the article

Product name:POLY (4-METHOXY STYRENE)

Cas No:24936-44-5

R&D Labs maybe for 24936-44-5

Suzhou HeChuang Chemical Co.,Ltd.

Contact:+86-512-88800520

Address:No.9 Guanchao Rd,Changshu Advanced Materials Industy Park
GenicBio Limited

Contact:+86-(0)21-3770 9035

Address:Room 301, Building 2, Meijiabang Road 1508, Shanghai China
Langchem

Contact:+86+21-58956006 15800617331

Address:402 Room, 150# Cailun Road, Zhangjiang high tech park, Shanghai
Zhejiang kehong chemical co., ltd

Contact:0086-575-85522000

Address:xiner center RD binhai industrial zone shaoxing zhejiang province P.R.China,312073
Deer Chemicals Co., Ltd.

Contact:+86-13666670345

Address:Agricultural Development Zone, Haining, Jiaxing, Zhejiang

Relevant to this article

Divergent Entry to Gelsedine-Type Alkaloids: Total Syntheses of (-)-Gelsedilam, (-)-Gelsenicine, (-)-Gelsedine, and (-)-Gelsemoxonine

Doi:10.1021/jacs.8b08127
(2018)
Converging Energy Transfer in Polynuclear Ru(II) Multiterpyridine Complexes: Significant Enhancement of Luminescent Properties

Doi:10.1021/acs.inorgchem.7b03040
(2018)
Mild and efficient method for the synthesis of nitriles

Doi:10.1081/SCC-120030750
(2004)
Endothelial protein C–targeting liposomes show enhanced uptake and improved therapeutic efficacy in human retinal endothelial cells

Doi:10.1167/iovs.18-23800
(2018)
Preparation of sodium borohydride by the reaction of MgH₂ with dehydrated borax through ball milling at room temperature

Doi:10.1016/S0925-8388(02)00872-1
(2003)
Head-to-tail intermolecular hydrogen bonding of OH and NH groups with fluoride

Doi:10.1002/cphc.201000463
(2011)

Article Doi