Perchloric Acid Catalyzed Homogeneous and Heterogeneous Addition of β-Dicarbonyl Compounds to Alcohols and Alkenes and Investigation of the Mechanism

2010 ◽  
Vol 75 (15) ◽  
pp. 5017-5030 ◽  
Author(s):  
Pei Nian Liu ◽  
Li Dang ◽  
Qing Wei Wang ◽  
Shu Lei Zhao ◽  
Fei Xia ◽  
...  
ChemInform ◽  
2010 ◽  
Vol 41 (50) ◽  
pp. no-no
Author(s):  
Pei Nian Liu ◽  
Li Dang ◽  
Qing Wei Wang ◽  
Shu Lei Zhao ◽  
Fei Xia ◽  
...  

1976 ◽  
Vol 10 (3) ◽  
pp. 363-364
Author(s):  
B. M. Savin ◽  
S. A. Kesler

2016 ◽  
Vol 81 (14) ◽  
pp. 6136-6141 ◽  
Author(s):  
Danbo Xie ◽  
Dan Shen ◽  
Qiliang Chen ◽  
Jiaqi Zhou ◽  
Xiaofei Zeng ◽  
...  

1996 ◽  
Vol 74 (7) ◽  
pp. 1366-1368 ◽  
Author(s):  
I. Egle ◽  
V. Gabelica ◽  
A.J. Kresge ◽  
T.T. Tidwell

Rates of conversion of 1-(tri-n-butylstannyl)-2-phenylethyne to phenylethyne in H2O and D2O solutions of perchloric acid were found to be proportional to acid concentration, giving the hydronium ion rate constant [Formula: see text] and the isotope effect [Formula: see text]. The magnitude of this isotope effect suggests that the reaction occurs by rate-determining hydron transfer to the substrate, producing a vinyl carbocation; this carbocation then loses its tributylstannyl group, giving phenylacetylene as the only detectable aromatic product. The hydronium ion rate constant, when compared to the rates of protonation of phenylethyne and 1-(trimethylsilyl)-2-phenylethyne, gives a β-stannyl stabilizing effect of δΔG≠ = 6.6 kcal mol−1 and a differential β-stannyl/β-silyl effect of δΔG≠ = 3.2 kcal mol−1. These stabilizations are very much smaller than previously reported β-stannyl effects. Possible reasons for the difference are suggested. Key words: β-stannyl effect, β-silyl effect, carbocation stabilization, protodemetalation.


Synlett ◽  
2013 ◽  
Vol 25 (02) ◽  
pp. 201-204 ◽  
Author(s):  
Philip Chan ◽  
Ciputra Tejo ◽  
Hui Yeo

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2012 ◽  
Vol 43 (32) ◽  
pp. no-no
Author(s):  
Mohd. Imran Ansari ◽  
Mohd. Kamil Hussain ◽  
Nisha Yadav ◽  
Puneet K. Gupta ◽  
K. Hajela

ChemInform ◽  
2012 ◽  
Vol 43 (52) ◽  
pp. no-no
Author(s):  
Srinivasa Reddy Mothe ◽  
Sherman Jun Liang Lauw ◽  
Prasath Kothandaraman ◽  
Philip Wai Hong Chan

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