159149-14-1

Basic information

• Product Name: Propanedinitrile, 6-oxabicyclo[3.1.0]hex-2-ylidene- (9CI)
• Synonyms: Propanedinitrile, 6-oxabicyclo[3.1.0]hex-2-ylidene- (9CI)
• CAS NO: 159149-14-1
• Molecular Formula: C8H6N2O
• Molecular Weight: 0
• Mol File: 159149-14-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Propanedinitrile, 6-oxabicyclo[3.1.0]hex-2-ylidene- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedinitrile, 6-oxabicyclo[3.1.0]hex-2-ylidene- (9CI)(159149-14-1)
• EPA Substance Registry System: Propanedinitrile, 6-oxabicyclo[3.1.0]hex-2-ylidene- (9CI)(159149-14-1)

Safety Data

• Hazardous Substances Data: 159149-14-1(Hazardous Substances Data)

Upstream product

• 130249-17-1 2,3-epoxycyclopentanone 
• 109-77-3 malononitrile 

Relevant articles and documents

1,3-Dipolar cycloadditions of photoinduced carbonyl ylides. Part 2. Photoreactions of α,β-unsaturated γ,δ-epoxy dinitriles and ethyl vinyl ether

Photoinduced carbonyl ylides B, C, E and F from the α,β-unsaturated γ,δ-epoxy dinitriles 2,3,5 and 6, respectively, undergo 1,3-dipolar cycloaddition with ethyl vinyl ether, leading to the tetrahydrofuran system. The cycloaddition proceeds with high regioselectivity affording predominantly the exo-adduct. However, the ylide from the mononitrile 1 and dinitrile 4 gives little or no adduct. The observed regioselectivity and the difference of the reactivity in these cycloadditions can be nicely accommodated in terms of semiempirical AMI calculations. The reactivity of the cycloaddition depends on the LUMO energy level and the C(γ),C(δ) distance of the ylide.