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A heterocumulene is a molecule or ion containing a chain of at least three double bonds between consecutive atoms, in which one or more atoms in the doubly
Heterocumulene
Chemical compound
precursors to nitrones and participate in [3+2] cycloadditions with various heterocumulenes to form substituted five-membered heterocycles. Some oxaziridines also
Oxaziridine
Hydrocarbon compound with 3 or more consecutive double bonds
electric dipole moment.) Cumulenes containing heteroatoms are called heterocumulenes; an example is carbon suboxide. The first reported synthesis of a butatriene
Cumulene
Chemical compound
gas. C3O can be classified as a ketene or an oxocumulene, a kind of heterocumulene. C3O has been detected by its microwave spectrum in the dark cold Taurus
Tricarbon_monoxide
Two-electron chemical bond where both electrons derive from the same atom
electron-sharing bonds) and minimizing formal charges would predict heterocumulene structures, and therefore linear geometries, for each of these compounds
Coordinate_covalent_bond
Chemical compound
substance that has been detected in outer space. Tricarbon monosulfide is a heterocumulene or thiocumulene, consisting of a straight chain of three carbon atoms
Tricarbon_monosulfide
Chemical compound
Ethylene dione or ethylenedione, also called dicarbon dioxide, carbon peroxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula
Ethylene_dione
Organic compound of the form >C=C=O
from diketene in ethanol.[citation needed] Ynol Thioketene Ketenimine Heterocumulene Miller R, Abaecherli C, Said A, Jackson B (2001). "Ketenes". Ullmann's
Ketene
Chemical compound
Carbon subsulfide is an organic, sulfur-containing chemical compound with the formula C3S2 and structure S=C=C=C=S. This deep red liquid is immiscible
Carbon_subsulfide
Chemical compound
Ethenedithione or ethylenedithone is an unstable chemical substance with formula S=C=C=S made from carbon and sulfur. Ethenedithione can exist as a gas
Ethenedithione
Chemical compound
double bonds in the ketene structure R1R2C=C=O, diphenyl ketene is a heterocumulene. The most important reaction of diphenyl ketene is the [2+2] cycloaddition
Diphenylketene
Chemical compound
Sulfene - related functional group with the formula H2C=SO2 Ethenone Heterocumulene Binne Zwanenburg (1989). "Sulfine Chemistry". Phosphorus, Sulfur, and
Sulfine
Chemical compound
with rapid bending (minimum đC2 ~ 170°), even in the solid state. A heterocumulene resonance form of carbon suboxide based on minimization of formal charges
Carbon_suboxide
Chemical compound
Isocyanogen, also known as cyanoisocyanogen, is a carbon nitride as well as a metastable isomer of cyanogen which has also been detected in the interstellar
Isocyanogen
that are of the form R2C=C=C=O. They are a member of the family of heterocumulenes (R2C=(C)n=O), and are often considered an unsaturated homolog of ketenes
Alkylidene_ketene
Chemical compound
Tetracarbon dioxide is an oxide of carbon, a chemical compound of carbon and oxygen, with chemical formula C4O2 or O=C=C=C=C=O. It can be regarded as butatriene
Tetracarbon_dioxide
Chemical compound
Pentacarbon dioxide, officially penta-1,2,3,4-tetraene-1,5-dione, is an oxide of carbon (an oxocarbon) with formula C5O2 or O=C=C=C=C=C=O. The compound
Pentacarbon_dioxide
Chemical compound
has a nonlinear CCCO backbone, in contrast to cumulenes, as well as heterocumulenes such as carbon suboxide. The barrier to backbone linearization is at
Propadienone
Chemical compound
2026. Ulrich, Henri (2 December 2012). Cycloaddition Reactions of Heterocumulenes. Elsevier. p. 176. ISBN 978-0-323-16276-0. Retrieved 14 January 2026
Sulfonyl_diisocyanate
Chemical compound
; Taylor, D.R. (1974). "Per- and Poly-fluorinated Olefins, Dienes, Heterocumulenes and Acetylenes". In Banks, R.E.; Barlow, M.G. (eds.). Fluorocarbon
Tribromofluoromethane
1. Insertion of carbon monoxide, isocyanides, carbon dioxide, and heterocumulenes into the V-C bond of Tris(mesityl)vanadium(III)" Organometallics 1993
Organovanadium_chemistry
Chemical compound
1. Insertion of carbon monoxide, isocyanides, carbon dioxide, and heterocumulenes into the V-C bond of tris(mesityl)vanadium(III)". Organometallics.
Trimesitylvanadium
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