Butenenitrile

The electrophilic addition of Br2 or Cl2 to 2,3-butadiene nitrile afforded 3,4-dihalo-2-butenenitriles [261]. 

The reaction of 2-cyano-2,3-butadienenitrile 572 with MeLi or HX afforded a,(i-unsaturated 2-cyano-3-substituted-2-butenenitrile 573 [263]. 

Butenenitrile (allyl cyanide) is isomerized by the CU2O—CNC complex to 2-butenenitrile and its dimer (248). The key intermediate is... 

In a formal sense, the reaction of ascorbic acid (11) with various electrophiles may also be regarded as an intramolecular conjugate addition with subsequent alkylation of the intermediate enolate ion. For example, the reaction of 11 with ( )-2-methyl-2-butenenitrile afforded the natural product piptosidin (12), together with its di-epimer 1351. In a quite similar fashion, leucodrin (14) and delesserin (15) were prepared from the corresponding benzyl alcohols52. 

An attempt to polymerize 2-methyl-2-butenenitrile, MBN, by first isomerizing to methylenebuteronitrile (eq 46) led to isomerization instead (eq 47). 

When a nitrile bearing an a-hydrogen such as a-sodiobenzyl cyanide reacts, an acyclic product, 2,3,4-triphenyl-2-butenenitrile, is obtained through rearrangement of a sulfenic acid intermediate to an alkene with extrusion of SO (Scheme 11). 

Angelic acid nitrile Angeliconitrile 2-Butenenitrile, 2-methyl-, (Z)- 2-Butenenitrile, 2-methyl-, (2Z)- Crotononitrile, 2-methyl-, (Z)- EINECS 243-496-6 HSDB 6156 (Z)-2-Methyl-2-butenenitrile 2-Methyl-cis-2-butenenitrile cis-2-Methyl-2-butenonitrile. 

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