A NEW MUSTARD OIL GLUCOSIDE SYNTHESIS: THE SYNTHESIS OF GLUCOTROPAEOLIN

1963 ◽  
Vol 41 (11) ◽  
pp. 2836-2838 ◽  
Author(s):  
M. H. Benn
Keyword(s):  
Double Bond ◽  
Mustard Oil ◽  
Nitrile Oxides ◽  
New Synthesis ◽  
Nitrogen Double Bond

A new synthesis of mustard oil glucosides is described, illustrated by the synthesis of glucotropaeolin. This synthesis, based on the reaction of thiols with nitrile oxides, leads to a conclusion concerning the stereochemistry about the carbon–nitrogen double bond in the mustard oil glucosides.

Configuration stability at the carbon-nitrogen double bond

1962 ◽  
Vol 3 (26) ◽  
pp. 1269-1274 ◽  
Author(s):  
D.Y. Curtin ◽  
C.G. McCarty
Keyword(s):  
Double Bond ◽  
Nitrogen Double Bond

Mechanisms of Nucleophilic Attack at Carbon Nitrogen Double-Bonds: The Reaction of Benzohydrazonoyl Halides With Amines

1987 ◽  
Vol 40 (10) ◽  
pp. 1777 ◽  
Author(s):  
AF Hegarty ◽  
P Rigopoulos ◽  
JE Rowe
Keyword(s):  
Double Bond ◽  
Nucleophilic Attack ◽  
Rate Data ◽  
Double Bonds ◽  
Nitrogen Double Bond

Rate data for the reaction of a series of benzohydrazonoyl halides with pyrrolidine and butan- 1-amine at 303 K are presented. Linear Hammett plots were obtained with each amine. The mechanism of the reactions and the stereochemical outcome of these displacements at the carbon-nitrogen double bond are discussed.

Metal-Free Addition of Boronic Acids to Silylnitronates

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 856-860
Author(s):  
Laurent El Kaïm ◽  
Mansour Dolé Kerim ◽  
Pakoupati Boyode ◽  
Julian Garrec
Keyword(s):  
Reaction Mechanism ◽  
Double Bond ◽  
Boronic Acids ◽  
Dft Study ◽  
Metal Free ◽  
Nitro Derivatives ◽  
Oxime Derivatives ◽  
Nitrogen Double Bond ◽  
First Time ◽  
Aryl Transfer

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives.

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