Studies on the Hurtley reaction

1974 ◽  
Vol 27 (10) ◽  
pp. 2209 ◽  
Author(s):  
KA Cirigottis ◽  
E Ritchie ◽  
WC Taylor

As a result of a large number of experiments on the Hurtley reaction the following tentative conclusions are drawn: (a) the best and most convenient solvent is ethanol; (b) the reaction succeeds best with aromatic o-bromocarboxylic acids although o-iodo acids can be expected to give low yields; (c) replacement of the carboxyl group by any other functional group prevents the reaction; (d) a copper species, probably copper(l), is an essential catalyst. The reactivity of 8-bromo-1-naphthoic acid, which is almost identical with that of o-bromobenzoic acid, is evidence against the intermediacy of a planar resonance hybrid structure. The geometry of the bromo acid-copper intermediate appears to be of paramount importance.

2021 ◽  
pp. 1-1
Author(s):  
Shashi Zhang ◽  
Haixia Liu ◽  
Yongzhi Fang ◽  
Min Li ◽  
Hao Ding ◽  
...  

1944 ◽  
Vol 22b (3) ◽  
pp. 56-65 ◽  
Author(s):  
H. L. Holmes ◽  
L. W. Trevoy

The method of Crowley and Robinson (5) for the synthesis of 6-methoxy-3,4-dihydro-2-naphthoic acid has been modified to provide an improved and general method for the synthesis of 3,4-dihydro-2-naphthoic acids. The 7-methoxy-3,4-dihydro-2-naphthoic acid and its ethyl ester have been shown to react with butadiene and 2,3-dimethylbutadiene to give 3-methoxy-5,8,9,10,13,14-hexahydrophenanthrene-14-carboxylic acid and its 6,7-dimethyl derivative. The relationship of these hydrophenanthrenes to possible degradation products of morphine and metathebainone has been discussed. An unsuccessful attempt was made to lengthen the C14-chain by converting the carboxyl group to an aldehyde group by the Rosenmund method followed by condensation with malonic acid. The projected conversion failed in the first stage.


Author(s):  
Ahmad Basheer ◽  
Ilan Marek

Carbocupration of α-heterosubstituted alkynes leads to the formation of stereodefined functionalized vinyl copper species as single isomer. Recent advances in the field show that a simple pre-association of the organometallic derivative with an additional polar functional group in the vicinity of the reaction center may completely change the stereochemical outcome of the reaction. Representative examples are given in this mini-review.


1973 ◽  
Vol 133 (2) ◽  
pp. 364-368 ◽  
Author(s):  
C. C. Kuenzle ◽  
M. H. Weibel ◽  
R. R. Pelloni ◽  
P. Hemmerich

A novel conformational structure of bilirubin is presented which obtains maximum stabilization through a system of four intramolecular hydrogen bonds. Two hydrogen bonds link oxygen and nitrogen atoms of each end ring to the contralateral carboxyl group. The proposed structure can explain a variety of uncommon features of bilirubin, and reconciles many seemingly contradictory hypotheses by accommodating them in individual structures which are mesomeric forms of one resonance hybrid. In the light of this newly conceived structure the following characteristics of bilirubin are re-evaluated: the stability of the compound, its reaction with diazomethane, the conformational behaviour of its dimethyl ester, its spectral properties, the chirality of the compound when complexed to serum albumin, and the structure of its metal chelates.


2015 ◽  
Vol 12 (1) ◽  
pp. 3575-3880
Author(s):  
Guosheng Wang ◽  
Jin Cai ◽  
Lei Li ◽  
Jian Song

The modification of peanut shell by nitric acid, sodium hydroxide, and epichlorohydrin have been conducted accordingly, andapplication in the purification of high purity boric acid from industry productshave been carry out, the result indicated that modification by epichlorohydrin was more effective than by nitric acid and by sodium hydroxide in the purification which the iron ion, sulfate ion, and chloridion can be removed simultaneously from industry boric acid, the analytical result by IR, SEM, and XRD confirmed that there are amount of hydroxyl and carboxyl group and ether bound in the modified peanut shell as functional group for adsorption of various metals ion and anions.


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