151231-67-3

Upstream product

• 57294-86-7 (E)-cinnamyl azide 
• 603-35-0 triphenylphosphine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 85669-63-2 (E)-cinnamyl diethyl phosphate 
• 85669-64-3 (Z)-diethyl (3-phenylallyl) phosphate 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 21040-45-9 Cinnamyl acetate 
• 103723-91-7 cinnamyl chloroformate 

Downstream Products

• 4335-60-8 (E)-cinnamylamine 
• 136844-01-4 2,2,3-Triphenyl-pent-4-enenitrile 
• 120990-23-0 N-(phenylmethylidene)-N-[(E)-3-phenylprop-2-enyl]amine 
• 158657-32-0 [1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-((E)-3-phenyl-allyl)-amine 
• 842172-35-4 [1-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(E)-ylidene]-((E)-3-phenyl-allyl)-amine 
• 842172-37-6 (3R,4R)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one 
• 842172-36-5 (3S,4S)-4-((3aR,5R,6R,6aS)-6-Iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-phenoxy-1-((E)-3-phenyl-allyl)-azetidin-2-one 
• 728033-64-5 (3R,4R)-3-Benzyloxy-4-((3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((E)-3-phenyl-allyl)-azetidin-2-one 
• 728033-61-2 (3S,4S)-3-Benzyloxy-4-((3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((E)-3-phenyl-allyl)-azetidin-2-one 
• 151231-86-6 2-(4-Chloro-phenyl)-N-((E)-3-phenyl-allyl)-2-(triphenyl-λ⁵-phosphanylidene)-acetamide 
• 151231-87-7 2-(4-Fluoro-phenyl)-N-((E)-3-phenyl-allyl)-2-(triphenyl-λ⁵-phosphanylidene)-acetamide 
• 151231-85-5 2-Phenyl-N-((E)-3-phenyl-allyl)-2-(triphenyl-λ⁵-phosphanylidene)-acetamide 

Relevant academic research and scientific papers

Synthesis of polycyclic β-lactams from D-glucose derived chiral template via substrate-controlled radical cyclization

A highly stereoselective and substrate-controlled synthesis of polycyclic β-lactams from D-glucose derived chiral template via intramolecular radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptenyl type radical cyclization with the radical acceptor allyl group at N-1 and the radical progenitor on a sugar moiety, anchored to the β-lactam ring at C-4. The mode of radical cyclization in N-propargyl substrates is highly stereospecific and controlled by the stereochemistry of the β-lactam ring.

A simple one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene: Synthesis of N1-cinnamyl azetidin-2-ones

A simple and efficient one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene and sodium azide is described. An application of cinnamyl azide for the synthesis of various N1 -cinnamyl azetidin-2-ones is also described.

An efficient one-pot conversion of alkyl bromides into imines via the Staudinger reaction

A new one-pot procedure for transforming primary alkyl bromides into the corresponding imines via the Staudinger reaction has been developed. Acetonitrile was found to be an excellent solvent for azidation as well as the reaction of organic azide with triphenylphosphine and a carbonyl compound.

Reaction of allyl iminophosphoranes with ketenes and acyl chlorides: One-pot preparation of 4-pentenenitriles

One-pot conversion of allylazides into 4-pentenenitriles 4 is achieved by sequential treatment of allyl azides with triphenylphosphine and the corresponding ketene under mild and neutral conditions. On the other hand, allyl iminophosphoranes and related react with arylacetic acid chlorides to give unexpectedly the phosphonium salts 5 which by treatment with base and then heating lead to 4-pentenenitriles 9.

Iminophosphorane-mediated one-pot conversion of allyl azides into α-allylated nitriles by a consecutive staudinger reaction/aza-wittig reaction/3-aza-claisen rearrangement process

One-pot conversion of allyl azides 1 into nitriles 3 under mild and neutral conditions is reported. The method involves sequential treatment of 1 with triphenylphosphine and the corresponding ketene to give 3.

Palladium(0)-Catalyzed Azidation of Allyl Esters. Selective Synthesis of Allyl Azides, Primary Allylamines, and Related Compounds

Palladium(0)-catalyzed reaction of allyl esters such as phosphates, carbonates, and carboxylates with sodium azide gives allyl azides.The azidation proceeds with retention of configuration at the allylic carbon.Optically active (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide (19) is obtained from (R)-(E)-(+)-4-phenyl-3-buten-2-yl acetate (18) stereoselectively.Sequential substitution of (Z)-4-acetoxy-2-buten-1-yl diethyl phosphate (24) with nucleophiles and subsequently azide ion gives (E)-4-substituted-2-buten-1-yl azides 27.The reaction of allyl azides with triphenylphosphine gives iminotriphenylphosphoranes, which are versatile synthetic intermediates of primary allylamines, N-allylamines, and N-allylamides.Treatment of allyl azides with triphenylphosphine and subsequently with aqueous ammonium solution gives primary allylamines.Other synthetic applications of allyl azides are also described.