THE SYNTHESIS OF ALKYLPHOSPHONOUS DICHLORIDES FROM ALUMINUM CHLORIDE – PHOSPHORUS TRICHLORIDE – ALKYL CHLORIDE COMPLEXES

1963 ◽  
Vol 41 (9) ◽  
pp. 2299-2302 ◽  
Author(s):  
B. J. Perry ◽  
J. B. Reesor ◽  
J. L. Ferron

In 1957, a new method for the synthesis of methylphosphonous dichloride, in high yield, by the reduction of the aluminum chloride – phosphorus trichloride – methyl chloride complex in diethyl phthalate solution by finely powdered antimony, was developed. That this is a general method for the synthesis of the more volatile alkylphosphonous dichlorides was demonstrated by the preparation, in good yield, of a series of compounds from the aluminum chloride – phosphorus trichloride complexes formed from ethyl chloride, n-propyl chloride, i-propyl chloride, n-butyl chloride, and s-butyl chloride. As expected, isomerization occurred in the case of the normal alkyl chlorides.

1980 ◽  
Vol 58 (12) ◽  
pp. 1198-1205 ◽  
Author(s):  
K. R. Fountain ◽  
Pamela Heinze ◽  
Mark Sherwood ◽  
Dave Maddex ◽  
Greg Gerhardt

Acylations of aromatic substrates with ketenes involve the reactivity of species similar to vinyl cations. Resonance stabilization of ketene – aluminum chloride complexes seems to make these complexes less reactive than corresponding vinyl cations.The kinetic isotope effect of the reaction with dimethylketene and benzene is 1.06, compatible with vinylcation cases, but not with acylation with CH3COBF4 types of electrophiles.Substrate specificity was determined from k (toluene)/k (benzene) values. It was 47.2 for dimethylketene and 173.7 for diphenylketene. The diphenylketene – aluminum chloride complex could be isolated.


1951 ◽  
Vol 29 (2) ◽  
pp. 162-165 ◽  
Author(s):  
A. Zlatkis ◽  
E. A. Smith

Both racemic forms of trans 2-chlorodecalin have been prepared and separated in pure form. The reaction between these chlorodecalins and ethylmagnesium bromide has been studied and two racemates of trans 2-ethyl decalin have been isolated. Some progress has been made in the preparation of the 9-chlorodecalins. A new method for converting cis decalin to trans decalin rapidly in high yield using tertiary butyl chloride and anhydrous aluminum chloride is indicated.


2012 ◽  
Vol 53 (3) ◽  
pp. 357-362 ◽  
Author(s):  
A. B. Arbuzov ◽  
V. A. Drozdov ◽  
M. O. Kazakov ◽  
A. V. Lavrenov ◽  
M. V. Trenikhin ◽  
...  

2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>


1983 ◽  
Vol 14 (12) ◽  
Author(s):  
C. M. MIKULSKI ◽  
S. COCCO ◽  
L. MATTUCCI ◽  
N. DEFRANCO ◽  
L. WEISS ◽  
...  

2004 ◽  
Vol 53 (12) ◽  
pp. 2881-2883 ◽  
Author(s):  
I. I. Ponomarev ◽  
Yu. Yu. Rybkin ◽  
E. I. Goryunov ◽  
P. V. Petrovskii ◽  
K. A. Lyssenko

2014 ◽  
Vol 118 (48) ◽  
pp. 27623-27630 ◽  
Author(s):  
Christopher J. Barile ◽  
Elizabeth C. Barile ◽  
Kevin R. Zavadil ◽  
Ralph G. Nuzzo ◽  
Andrew A. Gewirth

Synthesis ◽  
1971 ◽  
Vol 1971 (03) ◽  
pp. 139-140 ◽  
Author(s):  
J. B. KOSTER ◽  
G. J. TIMMERMANS ◽  
H. VAN BEKKUM

1971 ◽  
Vol 49 (12) ◽  
pp. 2064-2072 ◽  
Author(s):  
R. A. B. Bannard ◽  
N. C. C. Gibson ◽  
J. H. Parkkari

trans-2-Acetamidocyclohexanol (1; n = 2, R = CH3) on addition to thionyl chloride in chloroform at 0° was converted rapidly and quantitatively to D,L-2-methyl-4,5-cis-cyclohexanoöxazoline hydrochloride (2; n = 2, R = CH3) judging from shifts in the methyl proton resonances of the n.m.r. spectra of the amide and the reaction solution. The intermediate chlorosulfinate was estimated to have a half-life of less than 2.25 min. The oxazoline salt was isolated in 98% yield by sublimation of the crude product in vacuo and was identified by its i.r. and n.m.r. spectra and by its facile and almost quantitative hydrolysis to cis-2-aminocyclohexanol hydrochloride. The oxazoline salts 2 (n = 1, R = CH3, [Formula: see text] and n = 2, R = C6H5, [Formula: see text]) were readily obtained in 95 % yield or better by the same general method and it was shown that the trans-2-acetamidocyclanols are the preferred starting materials for conversion to cis-2-aminocyclanol derivatives by the thionyl chloride inversion reaction. The oxazoline bases 4 (n = 1, R = CH3, [Formula: see text] and n = 2, R = CH3, [Formula: see text]) were readily obtained in high yield from the corresponding salts and differences in the i.r. and n.m.r. spectral characteristics of the salts and bases are reported.


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