Mechanisms of alkoxide substitution reactions at the carbon-nitrogen double bond. Stereoelectronic control during nucleophilic substitution

1981 ◽  
Vol 46 (18) ◽  
pp. 3623-3629 ◽  
Author(s):  
James Elver Johnson ◽  
Elizabeth Ann Nalley ◽  
Charles Weidig ◽  
Mohammed Arfan
Keyword(s):  
Double Bond ◽  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Stereoelectronic Control ◽  
Nitrogen Double Bond

Mechanism of amine and amide ion substitution reactions at the carbon-nitrogen double bond

1985 ◽  
Vol 50 (18) ◽  
pp. 3348-3355 ◽  
Author(s):  
James Elver Johnson ◽  
Abdolkarim Ghafouripour ◽  
Mohammad Arfan ◽  
Susan L. Todd ◽  
Deborah A. Sitz
Keyword(s):  
Double Bond ◽  
Substitution Reactions ◽  
Ion Substitution ◽  
Nitrogen Double Bond

2-Azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis and nucleophilic substitution at the carbon–nitrogen double bond

1996 ◽  
Vol 74 (3) ◽  
pp. 287-294 ◽  
Author(s):  
Antonio Lorente ◽  
Marta Casillas ◽  
Pilar Gomez-Sal ◽  
Antonio Manzanero
Keyword(s):  
Double Bond ◽  
Nucleophilic Substitution ◽  
Key Words ◽  
Sodium Methoxide ◽  
Stereoselective Synthesis ◽  
X Ray Diffraction ◽  
Key Words 2 ◽  
X Ray ◽  
Nitrogen Double Bond

The synthesis of (E)-1-methoxy-2-azabuta-1,3-diene-4-carbonitriles was performed by methylation of N-alkenylamides 9 and 11. The Z isomers were obtained by treatment of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with sodium methoxide in methanol. We also describe the reactions of (E)-1-methylthio-2-azabuta-1,3-diene-4,4-dicarbonitriles with pyrrolidine, which afforded 1-(1-pyrrolidinyl) derivatives 20, 21, and 23. X-ray crystallographic analyses of 21 and 23 established the E stereochemistry of the C—N double bond. Key words: 2-azabuta-1,3-diene-4-carbonitriles: stereoselective synthesis, nucleophilic substitution and X-ray diffraction; N-alkenylamides: methylation.

ChemInform Abstract: MECHANISM OF AMINE AND AMIDE ION SUBSTITUTION REACTIONS AT THE CARBON-NITROGEN DOUBLE BOND

1985 ◽  
Vol 16 (52) ◽  
Author(s):  
J. E. JOHNSON ◽  
A. GHAFOURIPOUR ◽  
M. ARFAN ◽  
S. L. TODD ◽  
D. A. SITZ
Keyword(s):  
Double Bond ◽  
Substitution Reactions ◽  
Ion Substitution ◽  
Nitrogen Double Bond

Mechanisms and stereochemistry of amine substitution reactions at the carbon-nitrogen double bond

1992 ◽  
Vol 57 (17) ◽  
pp. 4648-4653 ◽  
Author(s):  
James Elver Johnson ◽  
Susan L. Todd ◽  
Susan M. Dutson ◽  
Abdolkarim Ghafouripour ◽  
Reidun M. Alderman ◽  
...  
Keyword(s):  
Double Bond ◽  
Substitution Reactions ◽  
Nitrogen Double Bond

Additions and Corrections - Mechanism of Amine and Amide Ion Substitution Reactions at the Carbon-Nitrogen Double Bond

1986 ◽  
Vol 51 (11) ◽  
pp. 2156-2156
Author(s):  
James Johnson ◽  
Abdolkarim Ghafouripour ◽  
Mohammad Arfan ◽  
Susan Todd ◽  
Deborah Sitz
Keyword(s):  
Double Bond ◽  
Substitution Reactions ◽  
Ion Substitution ◽  
Nitrogen Double Bond

The unexpected reactivity of 9-iodo-nido-carborane: from nucleophilic substitution reactions to the synthesis of tricobalt tris(dicarbollide) Na[4,4′,4′′-(MeOCH2CH2O)3-3,3′,3′′-Co3(μ3-O)(μ3-S)(1,2-C2B9H10)3]

2021 ◽  
Vol 50 (7) ◽  
pp. 2671-2688
Author(s):  
Marina Yu. Stogniy ◽  
Sergey A. Anufriev ◽  
Akim V. Shmal'ko ◽  
Sergey M. Antropov ◽  
Aleksei A. Anisimov ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions

An unusual reactivity of 9-iodo-nido-carborane [9-I-7,8-C2B9H11]− towards nucleophiles under strong basic conditions was revealed.

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