111571-84-7

Upstream product

• 2942-58-7 diethyl cyanophosphonate 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 2408-36-8 lithium cyanide 

Downstream Products

• 20068-10-4 (E)-4-phenyl-3-butenenitrile 
• 122421-75-4 (E)-2-styrylhexanenitrile 
• 122421-72-1 (Z)-4-phenyloct-2-enenitrile 
• 122421-74-3 (E)-4-Phenyl-oct-2-enenitrile 
• 113348-39-3 (1R,2R)-2-Cyano-1-methyl-2-((E)-styryl)-cyclopropanecarboxylic acid ethyl ester 
• 113348-39-3 (1S,2R)-2-Cyano-1-methyl-2-((E)-styryl)-cyclopropanecarboxylic acid ethyl ester 
• 111571-88-1 (Z)-4-diethylphosphonooxy-4-phenyl-2-butenenitrile 
• 111571-87-0 (E)-4-diethylphosphonooxy-4-phenyl-2-butenenitrile 
• 123346-77-0 (Z)-1-methyl-2-styrylcyclopropanecarboxylate 
• 123346-77-0 (E)-1-methyl-2-styrylcyclopropanecarboxylate 
• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 
• 113348-38-2 (Z)-ethyl-2-cyano-2-styrylcyclopropanecarboxylate 
• 113348-38-2 (E)-ethyl-2-cyano-2-styrylcyclopropanecarboxylate 

Relevant academic research and scientific papers

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.

Cyano-phosphorylation of aldehydes catalyzed by a nucleophilic N-heterocyclic carbene

The first method for cyano-phosphorylation of aldehydes with diethyl cyanophosphonate in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and KOt-Bu, as a nucleophilic catalyst, is described.

Allylic Rearrangement of Cyanophosphates. III. Reaction of Acyclic Enone Cyanophosphates

Boron trifluoride-catalyzed allylic rearrangement of α,β-unsaturated ketone cyanophosphates (2, 6 and 12) gave (Z)-4-diethylphosphonooxy-2-butenenitriles (3, 8 and 13), while α,β-unsaturated aldehyde cyanophosphates (17a-c) afforded (E)-4-diethylphosphonooxy-2-butenenitriles (18a-c) stereoselectively.The stereo- and regioselective reaction of 2 with several kinds of aromatics in the presence of boron trifluoride etherate afforded (Z)-4-aryl-2-methyl-2-butenenitriles (20) via the SN2' reaction.On the other hand, treatment of 2 with 1-substituted indoles in the presence of boron trifluoride etherate gave 1-amino-2-methylcarbazole derivatives (23a-c).Keywords-α,β-unsaturated ketone; α,β-unsaturated aldehyde; cyanophosphate; allylic rearrangement; boron trifluoride etherate; 2-butenenitrile derivative; SN2' reaction; 1-aminocarbazole derivative